Organic light-emitting devices

Abstract

The present specification provides an organic light-emitting device including a light-emitting layer.

Description

Technical Field

[0001] This specification relates to organic light emitting devices.

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2019-0157413 filed in the Korean Intellectual Property Office on November 29, 2019, the entire contents of which are incorporated herein by reference. Background Art

[0003] Generally, the organic light-emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy by using organic materials. An organic light-emitting device utilizing the organic light-emitting phenomenon generally has a structure including a positive electrode, a negative electrode, and an organic material layer therebetween. Here, in many cases, the organic material layer has a multilayer structure composed of different materials to improve the efficiency and stability of the organic light-emitting device. For example, the organic material layer may be composed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and the like. In such a structure of an organic light-emitting device, if a voltage is applied between the two electrodes, holes are injected into the organic material layer from the positive electrode and electrons are injected into the organic material layer from the negative electrode. When the injected holes and electrons meet each other, excitons are formed, and light is emitted when the excitons fall to the ground state again.

[0004] There is a continuing need to develop new materials for the aforementioned organic light-emitting devices.

[0005] [Citation List] (Patent Document 1) Korean Patent Application Publication No. 10-2015-0011347 Summary of the invention

[0006] Technical issues

[0007] This specification provides an organic light-emitting device.

[0008] Technical Solution

[0009] The present specification provides an organic light-emitting device including: a positive electrode; a negative electrode; and an organic material layer including a light-emitting layer disposed between the positive electrode and the negative electrode, wherein the light-emitting layer includes a compound represented by Formula 1 and a compound represented by the following Formula 2.

[0010]

[0011] In equation 1 and equation 2,

[0012] L1 to L3 are the same as or different from each other and are each independently a direct bond; or a substituted or unsubstituted arylene group,

[0013] Ar1 to Ar3 are the same as or different from each other and are each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

[0014] m is 0 or 1,

[0015] g1 is an integer from 0 to 7,

[0016] A1 to A3 are the same as or different from each other, and are each independently a monocyclic to polycyclic aromatic hydrocarbon ring; or a monocyclic to polycyclic aromatic heterocyclic ring,

[0017] R1 to R5 are the same as or different from each other, and are each 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 silyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthio group; or a substituted or unsubstituted amino group, or bond with an adjacent substituent to form a substituted or unsubstituted ring,

[0018] r1 is an integer from 0 to 4, r2 is an integer from 0 to 4, r3 is an integer from 0 to 3, and when r1 to r3 are each 2 or more, the substituents in the brackets are the same as or different from each other,

[0019] Formula 1 contains at least one deuterium, and

[0020] Formula 2 contains at least one deuterium.

[0021] Beneficial Effects

[0022] The organic light emitting device described in the present specification has a low driving voltage and has excellent efficiency characteristics and excellent lifespan by including the compound represented by Formula 1 and the compound represented by Formula 2 in a light emitting layer. BRIEF DESCRIPTION OF THE DRAWINGS

[0023] Figure 1 An organic light emitting device according to an exemplary embodiment of the present specification is shown.

[0024] [Explanation of Reference Numerals]

[0025] 1: Base

[0026] 2: Positive electrode

[0027] 3: Luminous layer

[0028] 4: Negative electrode

[0029] 5: Hole injection layer

[0030] 6: Hole transport layer

[0031] 7: Electron transport layer

[0032] 8: Electron injection layer DETAILED DESCRIPTION

[0033] Hereinafter, the present specification will be described in more detail.

[0034] The present specification provides an organic light-emitting device including a light-emitting layer, the light-emitting layer including a compound represented by Formula 1 and a compound represented by Formula 2. Specifically, the compound represented by Formula 1 and the compound represented by Formula 2 are included as a host and as a dopant, respectively.

[0035] The compound represented by Formula 2 has excellent light emitting characteristics due to a narrow full width at half maximum, but its lifespan performance is slightly insufficient.

[0036] The compound represented by Formula 1 has good hole and electron transport and injection, so that the driving voltage is stable and the photoluminescence quantum yield is high. Therefore, when the compound represented by Formula 1 is used as the host of the light-emitting layer of an organic light-emitting device, the organic light-emitting device has long service life and high efficiency characteristics.

[0037] In addition, the compound represented by Formula 1 and the compound represented by Formula 2 contain deuterium. When the compound contains deuterium, the efficiency and service life of the device are improved. Specifically, when hydrogen is replaced by deuterium, the chemical properties of the compound are hardly changed, but the physical properties of the deuterated compound are changed, so that the vibration energy level is reduced. The deuterium-substituted compound can prevent the reduction of quantum efficiency caused by the reduction of intermolecular van der Waals forces or the collision caused by intermolecular vibration. In addition, the CD bond can improve the stability of the compound.

[0038] The organic light-emitting device of the present invention may include the compound represented by Formula 1 and the compound represented by Formula 2 at the same time, thereby improving the service life problem while maintaining the excellent light-emitting characteristics of the compound of Formula 2.

[0039] The compounds of Formula 1 and Formula 2 containing deuterium can be prepared by a well-known deuteration reaction. According to an exemplary embodiment of the present specification, the compounds represented by Formula 1 and Formula 2 can be formed using a deuterated compound as a precursor, or deuterium can be introduced into the compound via a hydrogen-deuterium exchange reaction using a deuterated solvent in the presence of an acid catalyst.

[0040] In the present specification, the deuterium substitution rate of a compound means "(the number of deuterium contained in the compound) / (the maximum number of hydrogens which the compound can have)".

[0041] In the present specification, N% substitution with deuterium means that N% of available hydrogens in the corresponding structure are substituted with deuterium. For example, 25% substitution with deuterium of dibenzofuran means that two of the eight hydrogens of dibenzofuran are substituted with deuterium.

[0042] In this specification, the degree of deuteration can be determined by methods such as nuclear magnetic resonance spectroscopy ( 1 The amount of the product can be determined by known methods such as H NMR) or GC / MS.

[0043] In Formula 1 and Formula 2 of the present specification, even when the substituent to be substituted is not specified in detail, deuterium-substituted includes those substituted with deuterium.

[0044] In this manual, * or It means fused or connected parts.

[0045] In this specification, Cn means n carbon atoms.

[0046] In the present specification, "Cn-Cm" means "n to m carbon atoms".

[0047] Examples of the substituent in the present specification will be described below, but are not limited thereto.

[0048] The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is changed into another substituent, and the position to be substituted is not limited as long as the position is a position where a hydrogen atom is substituted (i.e., a position where a substituent can be substituted), and when two or more are substituted, the two or more substituents may be the same or different from each other.

[0049] In the present specification, the term "substituted or unsubstituted" means substituted with one or two or more substituents selected from the following: deuterium; halogen group; cyano group (-CN); silyl group; boron group; alkyl group; cycloalkyl group; aryl group; and heterocyclic group, substituted with a substituent in which two or more substituents are connected among the exemplified substituents, or having no substituent. For example, "a substituent in which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may also be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.

[0050] In an exemplary embodiment of the present invention, "substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of: deuterium; a halogen group; a cyano group (-CN); a silyl group; a C1-C20 alkyl group; a C3-C60 cycloalkyl group; a C6-C60 aryl group; and a C2-C60 heterocyclic group, substituted with a substituent in which two or more groups selected from the above group are connected, or having no substituent.

[0051] In an exemplary embodiment of the present invention, "substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of: deuterium; a halogen group; a cyano group (-CN); a silyl group; a C1-C10 alkyl group; a C3-C30 cycloalkyl group; a C6-C30 aryl group; and a C2-C30 heterocyclic group, substituted with a substituent in which two or more groups selected from the above group are connected, or having no substituent.

[0052] In an exemplary embodiment of the present invention, "substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of: deuterium; a halogen group; a cyano group (-CN); a silyl group; a C1-C6 alkyl group; a C3-C20 cycloalkyl group; a C6-C20 aryl group; and a C2-C20 heterocyclic group, substituted with a substituent in which two or more groups selected from the above group are connected, or having no substituent.

[0053] In the present specification, the fact that two or more substituents are linked means that the hydrogen of any substituent becomes another substituent. For example, an isopropyl group and a phenyl group may be linked to each other to form a substituent.

[0054] In the present specification, the case where three substituents are connected to each other includes not only the case where (substituent 1)-(substituent 2)-(substituent 3) are connected to each other in sequence, but also the case where (substituent 2) and (substituent 3) are connected to (substituent 1). For example, two phenyl groups and an isopropyl group may be connected to each other to form a substituent. The same applies to the case where four or more substituents are bonded to one another.

[0055] In the present specification, "substituted by A or B" includes not only the case of being substituted by A alone or by B alone, but also the case of being substituted by both A and B.

[0056] In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 1 to 20. Specifically, the number of carbon atoms is more preferably 1 to 10; or 1 to 6. Specific examples thereof include: methyl; ethyl; propyl; n-propyl; isopropyl; butyl; n-butyl; isobutyl; tert-butyl; sec-butyl; 1-methylbutyl; 2-methylbutyl; 1-ethylbutyl; pentyl; n-pentyl; isopentyl; neopentyl; tert-pentyl; hexyl; n-hexyl; 1-methylpentyl; 2-methylpentyl; 4-methylpentyl; 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-ethylpropyl; tert-pentyl (1,1-dimethylpropyl); isohexyl; 2-methylpentyl; 4-methylhexyl; 5-methylhexyl; and the like, but are not limited thereto.

[0057] In the present specification, an alkoxy group is an alkyl group in which an alkyl group is bonded to an oxygen atom, an alkylthio group is an alkyl group in which an alkyl group is bonded to a sulfur atom, and the above description of the alkyl group can be applied to the alkyl groups of the alkoxy group and the alkylthio group.

[0058] In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 2 to 30, 2 to 20, 2 to 10, or 2 to 5. Specific examples thereof 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, stilbene, styryl, and the like, but are not limited thereto.

[0059] In the present specification, cycloalkyl is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the carbon number of cycloalkyl is 3 to 30. According to another exemplary embodiment, the carbon number of cycloalkyl is 3 to 20. According to another exemplary embodiment, the carbon number of cycloalkyl is 3 to 6. Cycloalkyl includes not only monocyclic groups, but also bicyclic groups such as bridged rings, condensed rings and spiro rings. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, etc., but are not limited thereto.

[0060] In this specification, cycloolefin is a cyclic group having a double bond present in a hydrocarbon ring, but is not aromatic, and its carbon number is not particularly limited, but may be 3 to 60, and may be 3 to 30 according to an exemplary embodiment. Cycloolefin includes not only monocyclic groups, but also bicyclic groups such as bridged rings, condensed rings and spiro rings. Examples of cycloolefins include cyclopropene, cyclobutene, cyclopentene, cyclohexene, etc., but are not limited thereto.

[0061] In this specification, a silyl group can be represented by the formula -SiY 11 Y 12 Y 13 indicates that, and Y 11 , Y 12 and Y 13 Each of them may be hydrogen; a substituted or unsubstituted alkyl; or a substituted or unsubstituted aryl. Specific examples of the silyl group include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc., but are not limited thereto.

[0062] In the present specification, the amine group may be selected from -NH2; alkylamine group; alkylarylamine group; arylamine group; arylheteroarylamine group; alkylheteroarylamine group; and heteroarylamine group, and the number of carbon atoms thereof is not particularly limited, but is preferably 1 to 60. In the case of an arylamine group, the number of carbon atoms thereof is 6 to 60. According to another exemplary embodiment, the number of carbon atoms of the arylamine group is 6 to 40. Specific examples of the amino group include methylamino; dimethylamino; ethylamino; diethylamino; phenylamino; naphthylamino; biphenylamino; anthracenylamino; 9-methylanthrylamino; diphenylamino; N-phenylnaphthylamino; ditolylamino; N-phenyltolylamino; triphenylamino; N-phenylbiphenylamino; N-phenylnaphthylamino; N-biphenylnaphthylamino; N-naphthylfluorenylamino; N-phenylphenanthrenylamino; N-biphenylphenanthrenylamino; N-phenylfluorenylamino; N-phenylterphenylamino; N-phenanthrenylfluorenylamino; N-biphenylfluorenylamino; N-(4-(tert-butyl)phenyl)-N-phenylamino; N,N-bis(4-(tert-butyl)phenyl)amine; N,N-bis(3-(tert-butyl)phenyl)amine, and the like, but are not limited thereto.

[0063] In the present specification, the alkylamine group means an amine group in which N of the amine group is substituted with an alkyl group, and includes a dialkylamine group, an alkylarylamine group, and an alkylheteroarylamine group.

[0064] In the present specification, the arylamine group means an amine group in which N of the amine group is substituted with an aryl group, and includes a diarylamine group, an arylheteroarylamine group, and an alkylarylamine group.

[0065] In the present specification, the heteroarylamine group means an amine group in which N of the amine group is substituted with a heteroaryl group, and includes a diheteroarylamine group, an arylheteroarylamine group, and an alkylheteroarylamine group.

[0066] In the present specification, the alkylarylamine group means an amine group in which N of the amine group is substituted with an alkyl group and an aryl group.

[0067] In the present specification, the arylheteroarylamine group means an amine group in which N of the amine group is substituted with an aryl group and a heteroaryl group.

[0068] In the present specification, the alkylheteroarylamine group means an amine group in which N of the amine group is substituted with an alkyl group and a heteroaryl group.

[0069] In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the number of carbon atoms of the aryl group is 6 to 30. According to an exemplary embodiment, the number of carbon atoms of the aryl group is 6 to 20. Examples of monocyclic aryl groups as aryl groups include phenyl, biphenyl, terphenyl, etc., but are not limited thereto. Examples of polycyclic aryl groups include naphthyl, anthracenyl, phenanthrenyl, pyrenyl, perylenyl, triphenylene, fluorenyl, etc., but are not limited thereto.

[0070] In the present specification, the carbon atom (C) No. 9 of the fluorenyl group may be substituted with an alkyl group, an aryl group, or the like, and two substituents may be bonded to each other to form a spiro ring structure such as cyclopentane or fluorene.

[0071] In this specification, substituted aryl can also include a form in which an aliphatic ring is fused to the aryl. For example, substituted aryl includes tetrahydronaphthyl, dihydroindenyl and dihydroanthracenyl having the following structure. In the following structure, one carbon of the benzene ring can be connected to another position.

[0072]

[0073] In the present specification, the condensed hydrocarbon ring group means a condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and is a form in which the aromatic hydrocarbon ring and the aliphatic hydrocarbon ring are condensed. Examples of the condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring include tetrahydronaphthyl, dihydroindenyl and dihydroanthracenyl, but are not limited thereto.

[0074] In the present specification, the alkylaryl group means an aryl group substituted with an alkyl group, and a substituent other than the alkyl group may be further bonded.

[0075] In the present specification, an arylalkyl group means an alkyl group substituted with an aryl group, and a substituent other than the aryl group may be further bonded.

[0076] In the present specification, aryloxy is a group in which an aryl group is connected to an oxygen atom, arylthio is a group in which an aryl group is connected to a sulfur atom, and the above description of aryl can be applied to the aryl groups of aryloxy and arylthio. The aryl of aryloxy is the same as the above examples of aryl. Specifically, examples of aryloxy include phenoxy, p-tolyloxy, m-tolyloxy, 3,5-dimethyl-phenoxy, 2,4,6-trimethylphenoxy, p-tert-butylphenoxy, 3-biphenyloxy, 4-biphenyloxy, 1-naphthyloxy, 2-naphthyloxy, 4-methyl-1-naphthyloxy, 5-methyl-2-naphthyloxy, 1-anthraceneoxy, 2-anthraceneoxy, 9-anthraceneoxy, 1-phenanthrenoxy, 3-phenanthrenoxy, 9-phenanthrenoxy, etc., examples of arylthio include phenylthio, 2-methylphenylthio, 4-tert-butylphenylthio, etc., but examples are not limited thereto.

[0077] In the present specification, the heterocyclic group is a ring group containing one or more of N, O, P, S, Si and Se as a heteroatom, and the number of carbon atoms thereof is not particularly limited, but is preferably 2 to 60. According to an exemplary embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. According to an exemplary embodiment, the number of carbon atoms of the heterocyclic group is 2 to 20. Examples of the heterocyclic group include pyridyl; quinolyl; thienyl; dibenzothienyl; furyl; dibenzofuranyl; naphthobenzofuranyl; carbazolyl; benzocarbazolyl; naphthobenzothienyl; dibenzothirolyl; naphthobenzothirolyl; hexahydrocarbazolyl; dihydroacridinyl; dihydrodibenzoazasilyl; phenanthrenyl; oxazine; phenothiazine; dihydrodibenzazasilyl; spiro(dibenzosilole-dibenzazasilane) group; spiro(acridine-fluorene) group, and the like, but are not limited thereto.

[0078]

[0079] In the present specification, the above description of the heterocyclic group can be applied to the heteroaryl group, except that the heteroaryl group is aromatic.

[0080] In this specification, an aromatic hydrocarbon ring means a hydrocarbon ring in which the π electrons are completely conjugated and planar, and the description of an aryl group can be applied to an aromatic hydrocarbon ring, except that the aromatic hydrocarbon ring is divalent. The number of carbon atoms in the aromatic hydrocarbon ring may be 6 to 60; 6 to 30; 6 to 20; or 6 to 10.

[0081] In the present specification, an aliphatic hydrocarbon ring has a bonding structure of a ring and means a non-aromatic ring. Examples of the aliphatic hydrocarbon ring include a cycloalkyl group or a cycloolefin group, and the above description of the cycloalkyl group or the cycloalkenyl group can be applied to the aliphatic hydrocarbon ring, except that the aliphatic hydrocarbon ring is divalent. The number of carbon atoms of the aliphatic hydrocarbon ring may be 3 to 60; 3 to 30; 3 to 20; 3 to 10; 5 to 50; 5 to 30; 5 to 20; 5 to 10; or 5 and 6. In addition, the substituted aliphatic hydrocarbon ring also includes an aliphatic hydrocarbon ring in which an aromatic ring is condensed.

[0082] In the present specification, the condensed ring of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring means that the aromatic hydrocarbon ring and the aliphatic hydrocarbon ring form a condensed ring. Examples of the condensed ring of an aromatic ring and an aliphatic ring include 1,2,3,4-tetrahydronaphthyl, 2,3-dihydro-1H-indenyl, etc., but are not limited thereto.

[0083] In this specification, "adjacent" groups may mean substituents that replace atoms directly connected to atoms substituted by corresponding substituents, substituents that are arranged to be closest to the corresponding substituents in space, or other substituents that replace atoms substituted by corresponding substituents. For example, two substituents substituted at ortho positions in a benzene ring and two substituents that replace the same carbon in an aliphatic ring may be interpreted as groups "adjacent" to each other. In addition, substituents (four in total) connected to two consecutive carbons in an aliphatic ring may be interpreted as "adjacent" groups.

[0084] In the present specification, “adjacent groups bond to each other to form a ring” in a substituent means that the substituent bonds to the adjacent group to form a substituted or unsubstituted hydrocarbon ring; or a substituted or unsubstituted heterocyclic ring.

[0085] In the present specification, "a five-membered ring or a six-membered ring formed by bonding adjacent groups" means that the ring including the substituents participating in the ring formation is five-membered or six-membered. Another ring condensed with the ring including the substituents participating in the ring formation may be included.

[0086] In the present specification, when a substituent of an aromatic hydrocarbon ring or an aryl group bonds to an adjacent substituent to form an aliphatic hydrocarbon ring, the aliphatic hydrocarbon ring includes two π electrons (carbon-carbon double bond) of the aromatic hydrocarbon ring or the aryl group even if a double bond is not specified.

[0087] In the present specification, the above description of the aryl group can be applied to the arylene group, except that the arylene group is divalent.

[0088] In the present specification, the above description of the cycloalkyl group can be applied to the cycloalkylene group, except that the cycloalkylene group is divalent.

[0089] Hereinafter, Formula 1 will be described.

[0090] This specification provides a compound represented by the following Formula 1.

[0091] [Formula 1]

[0092]

[0093] In formula 1,

[0094] L1 to L3 are the same as or different from each other and are each independently a direct bond; or a substituted or unsubstituted arylene group,

[0095] Ar1 to Ar3 are the same as or different from each other and are each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

[0096] m is 0 or 1,

[0097] g1 is an integer from 0 to 7,

[0098] Formula 1 contains at least one deuterium.

[0099] When m is 0, hydrogen or deuterium is attached to the -L3-Ar3 position.

[0100] D stands for deuterium.

[0101] In an exemplary embodiment of the present specification, -L1-Ar1 and -L2-Ar2 are different from each other.

[0102] In an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a direct bond; or a substituted or unsubstituted C6-C30 arylene group.

[0103] In an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; or a substituted or unsubstituted naphthylene group.

[0104] In an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a direct bond; a phenylene group; or a naphthylene group.

[0105] In an exemplary embodiment of the present specification, Ar1 includes at least one deuterium.

[0106] In an exemplary embodiment of the present specification, L1 includes at least one deuterium.

[0107] In an exemplary embodiment of the present specification, L2 includes at least one deuterium.

[0108] In an exemplary embodiment of the present specification, L3 includes at least one deuterium.

[0109] In an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a direct bond or any one selected from the following structures.

[0110]

[0111] In the structure, D means deuterium, k1 is an integer from 0 to 4, and k2 is an integer from 0 to 6.

[0112] In an exemplary embodiment of the present specification, k1 is an integer of 1 to 4.

[0113] In an exemplary embodiment of the present specification, k2 is an integer of 1 to 6.

[0114] In an exemplary embodiment of the present specification, k1 is 4.

[0115] In an exemplary embodiment of the present specification, k2 is 6.

[0116] In an exemplary embodiment of the present specification, Ar1 to Ar3 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0117] In an exemplary embodiment of the present specification, Ar1 to Ar3 are the same as or different from each other, and are each independently a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C2-C30 heteroaryl group.

[0118] In an exemplary embodiment of the present specification, Ar1 to Ar3 are the same as or different from each other, and are each independently a C6-C30 aryl group which is unsubstituted or substituted with a C1-C10 alkyl group or a C1-C30 trialkylsilyl group; or a C2-C30 heteroaryl group which is unsubstituted or substituted with a C6-C30 aryl group.

[0119] In an exemplary embodiment of the present specification, Ar1 to Ar3 are the same as or different from each other, and are each independently a C6-C30 aryl group; or a C2-C30 heteroaryl group which is unsubstituted or substituted with a C6-C30 aryl group.

[0120] In an exemplary embodiment of the present specification, Ar1 to Ar3 are the same as or different from each other, and are each independently phenyl; biphenyl; naphthyl; phenanthryl; triphenylene; fluoranthenyl; pyrenyl; dibenzofuranyl which is unsubstituted or substituted with a C6-C20 aryl group; dibenzothienyl which is unsubstituted or substituted with a C6-C20 aryl group; naphthobenzofuranyl which is unsubstituted or substituted with a C6-C20 aryl group; or naphthobenzothienyl which is unsubstituted or substituted with a C6-C20 aryl group.

[0121] In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a phenyl group; or a biphenyl group.

[0122] In an exemplary embodiment of the present specification, Ar1 and Ar2 are naphthyl; phenanthryl; triphenylene; fluoranthenyl; or pyrene.

[0123] In an exemplary embodiment of the present specification, at least one of Ar1 and Ar2 is a dibenzofuranyl group which is unsubstituted or substituted with a C6-C20 aryl group; or a naphthyl group.

[0124] In an exemplary embodiment of the present specification, at least one of Ar1 and Ar2 is a dibenzofuranyl group which is unsubstituted or substituted with a C6-C20 aryl group; a naphthobenzofuranyl group which is unsubstituted or substituted with a C6-C20 aryl group; or a naphthobenzothienyl group which is unsubstituted or substituted with a C6-C20 aryl group.

[0125] In an exemplary embodiment of the present specification, at least one of Ar1 and Ar2 is a naphthyl group.

[0126] In an exemplary embodiment of the present specification, at least one of Ar1 and Ar2 is a dibenzofuranyl group substituted with a C6-C20 aryl group; a dibenzothienyl group substituted with a C6-C20 aryl group; or a naphthyl group.

[0127] In an exemplary embodiment of the present specification, at least one of Ar1 and Ar2 is 1-dibenzofuranyl substituted with a C6-C20 aryl group; 2-dibenzofuranyl substituted with a C6-C20 aryl group; 3-dibenzofuranyl substituted with a C6-C20 aryl group; 4-dibenzofuranyl substituted with a C6-C20 aryl group; 1-naphthyl; or 2-naphthyl.

[0128] In an exemplary embodiment of the present specification, at least one of Ar1 and Ar2 is a phenyl group; a dibenzofuranyl group substituted with a biphenyl group or a naphthyl group; a 1-naphthyl group; or a 2-naphthyl group.

[0129] In an exemplary embodiment of the present specification, Ar3 is a C6-C30 aryl group; or a C2-C30 heteroaryl group which is unsubstituted or substituted with a C6-C30 aryl group.

[0130] In an exemplary embodiment of the present specification, Ar3 is a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a triphenylene group, a fluoranthenyl group, a pyrenyl group, a dibenzofuranyl group substituted with a C6-C20 aryl group, or a dibenzothienyl group substituted with a C6-C20 aryl group.

[0131] In an exemplary embodiment of the present specification, Ar1 includes at least one deuterium.

[0132] In an exemplary embodiment of the present specification, Ar1 includes at least one deuterium.

[0133] In an exemplary embodiment of the present specification, Ar2 includes at least one deuterium.

[0134] In an exemplary embodiment of the present specification, Ar3 includes at least one deuterium.

[0135] In an exemplary embodiment of the present specification, m is 0.

[0136] When m is 0, Equation 1 is one selected from the following structural formulas.

[0137]

[0138] In an exemplary embodiment of the present specification, m is 1.

[0139] In an exemplary embodiment of the present specification, g1 is 1 or greater. In another exemplary embodiment, g1 is 2 or greater. In yet another exemplary embodiment, g1 is 3 or greater. In yet another exemplary embodiment, g1 is 4 or greater. In yet another exemplary embodiment, g1 is 5 or greater. In yet another exemplary embodiment, g1 is 6 or greater. In yet another exemplary embodiment, g1 is 7.

[0140] In an exemplary embodiment of the present specification, g1 is 7, m is 0, and -L3-Ar3 is deuterium.

[0141] In an exemplary embodiment of the present specification, Formula 1 is deuterated by 30% or more. In another exemplary embodiment, Formula 1 is deuterated by 40% or more. In yet another exemplary embodiment, Formula 1 is deuterated by 50% or more. In yet another exemplary embodiment, Formula 1 is deuterated by 60% or more. In yet another exemplary embodiment, Formula 1 is deuterated by 70% or more. In yet another exemplary embodiment, Formula 1 is deuterated by 80% or more. In yet another exemplary embodiment, Formula 1 is deuterated by 90% or more. In yet another exemplary embodiment, Formula 1 is deuterated by 100%.

[0142] In an exemplary embodiment of the present specification, Formula 1 includes at least one hydrogen. That is, Formula 1 is deuterated by less than 100%.

[0143] In an exemplary embodiment of the present specification, Formula 1 is any one selected from the following compounds. Specifically, this case is a case where m is 0.

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177] In an exemplary embodiment of the present specification, Formula 1 is any one selected from the following compounds. Specifically, this case is a case where m is 1.

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189] Hereinafter, Formula 2 will be described.

[0190] This specification provides a compound represented by the following Formula 2.

[0191] [Formula 2]

[0192]

[0193] In formula 2,

[0194] A1 to A3 are the same as or different from each other, and are each independently a monocyclic to polycyclic aromatic hydrocarbon ring; or a monocyclic to polycyclic aromatic heterocyclic ring,

[0195] R1 to R5 are the same as or different from each other, and are each 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 silyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthio group; or a substituted or unsubstituted amino group, or bond with an adjacent substituent to form a substituted or unsubstituted ring,

[0196] r1 is an integer from 0 to 4, r2 is an integer from 0 to 4, r3 is an integer from 0 to 3, and when r1 to r3 are each 2 or more, the substituents in the brackets are the same as or different from each other, and

[0197] Formula 2 contains at least one deuterium.

[0198] In an exemplary embodiment of the present specification, when r1 is 2 or greater, a plurality of R1s are identical or different from each other. In another exemplary embodiment, when r2 is 2 or greater, a plurality of R2s are identical or different from each other. In yet another exemplary embodiment, when r3 is 2 or greater, a plurality of R3s are identical or different from each other.

[0199] In an exemplary embodiment of the present specification, Formula 2 is deuterated by 30% or more. In another exemplary embodiment, Formula 2 is deuterated by 40% or more. In yet another exemplary embodiment, Formula 2 is deuterated by 50% or more. In yet another exemplary embodiment, Formula 2 is deuterated by 60% or more. In yet another exemplary embodiment, Formula 2 is deuterated by 70% or more. In yet another exemplary embodiment, Formula 2 is deuterated by 80% or more. In yet another exemplary embodiment, Formula 2 is deuterated by 90% or more. In yet another exemplary embodiment, Formula 2 is deuterated by 100%.

[0200] In an exemplary embodiment of the present specification, in Formula 2, deuterium is connected to or a substituent substituted by deuterium is connected to the para position relative to B (boron). For example, in the following structure, deuterium or a substituent substituted by deuterium can be connected to one or more of the positions represented by the dotted line. The position is not limited to the dotted position of the following structure, and deuterium or a substituent substituted by deuterium can be connected to the position, as long as the position can be interpreted as a position relative to B (boron). In this case, the substituent substituted by deuterium can be an alkyl substituted by deuterium, an aryl substituted by deuterium, an arylamine substituted by deuterium, or a heterocyclic group substituted by deuterium.

[0201]

[0202] In an exemplary embodiment of the present specification, in Formula 2, deuterium is connected to or a substituent substituted by deuterium is connected to the para position relative to N (nitrogen). For example, in the following structure, deuterium or a substituent substituted by deuterium is connected to one or more of the positions represented by the dotted line. The position is not limited to the dotted position of the following structure, and in the amine group (arylamine group, heteroarylamine group, etc.) included in Formula 2 or the substituent of Formula 2-A, deuterium or a substituent substituted by deuterium is connected to the para position relative to N (nitrogen). In this case, the substituent substituted by deuterium can be an alkyl substituted by deuterium, an aryl substituted by deuterium, an arylamine group substituted by deuterium, or a heterocyclic group substituted by deuterium.

[0203]

[0204] As described above, when deuterium or a substituent substituted with deuterium is attached to the para position relative to B (boron) or the para position relative to N (nitrogen), the long life characteristics of the device are improved.

[0205] In an exemplary embodiment of the present specification, Formula 2 includes at least one hydrogen.

[0206] In an exemplary embodiment of the present specification, all sites where hydrogen is bonded to the aromatic ring of Formula 2 are substituted with deuterium.

[0207] In an exemplary embodiment of the present specification, all sites where hydrogen is bonded to the aromatic hydrocarbon ring of Formula 2 are substituted with deuterium.

[0208] In an exemplary embodiment of the present specification, Formula 2 is represented by the following Formula 201.

[0209] [Formula 201]

[0210]

[0211] In formula 201,

[0212] Definitions of R1 to R3 and r1 to r3 are the same as those defined in Formula 2,

[0213] R6 and R7 are the same as or different from each other, and are each 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 silyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthio group; or a substituted or unsubstituted amine group, or bond with an adjacent substituent to form a substituted or unsubstituted ring, and

[0214] R6 and R7 are integers of 0 to 5, and when R6 to R7 are 2 or more, the substituents in the brackets are the same as or different from each other.

[0215] In an exemplary embodiment of the present specification, Formula 2 is represented by the following Formula 202 or Formula 203.

[0216] [Formula 202]

[0217]

[0218] [Formula 203]

[0219]

[0220] In equations 202 and 203,

[0221] Definitions of R1 to R3, r1, and r3 are the same as those defined in Formula 2,

[0222] Y2 to Y4 are the same as or different from each other and are each independently C or Si,

[0223] A21 to A32, R6, and Z1 to Z6 are the same as or different from each other, and are each 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 silyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthio group; or a substituted or unsubstituted amino group, or bond with an adjacent substituent to form a substituted or unsubstituted ring,

[0224] p2 to p4 are each 0 or 1,

[0225] r6 is an integer from 0 to 5, and

[0226] r1′ and r2′ are integers of 0 to 3, and when r6, r1′ and r2′ are each 2 or more, the substituents in the brackets are the same as or different from each other.

[0227] In an exemplary embodiment of the present specification, that is, in an organic light-emitting device, at least one of A1 and A2 is represented by the following formula 2-C:

[0228] [Formula 2-C]

[0229]

[0230] In Formula 2-C, * is a position fused with Formula 2, X is N(Ra1); O; or S, and Ra1 is a substituted or unsubstituted aryl group.

[0231] In an exemplary embodiment of the present specification, Formula 2 is represented by any one selected from the following Formula 204 to Formula 207.

[0232] [Formula 204]

[0233]

[0234] [Formula 205]

[0235]

[0236] [Formula 206]

[0237]

[0238] [Formula 207]

[0239]

[0240] In equations 204 to 207,

[0241] Definitions of R1 to R5 and r1 to r3 are the same as those defined in Formula 2,

[0242] X1 and X2 are the same as or different from each other and are each independently N(Ra1); O; or S, and

[0243] Ra1 are the same as or different from each other and are each 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 silyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthio group; or a substituted or unsubstituted amino group, or bond with an adjacent substituent to form a substituted or unsubstituted ring.

[0244] In an exemplary embodiment of the present specification, Formula 2 is represented by the following Formula 208.

[0245] [Formula 208]

[0246]

[0247] In formula 208,

[0248] The definitions of R1 to R5, and r3 are the same as those defined in Formula 2,

[0249] Y5 is C or Si,

[0250] Z7 and Z8 are the same as or different from each other, and are each 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 silyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthio group; or a substituted or unsubstituted amino group, or bond with an adjacent substituent to form a substituted or unsubstituted ring, and

[0251] r1′ is an integer from 0 to 3, r2′ is an integer from 0 to 3, and when r1′ and r2′ are each 2 or more, the substituents in the brackets are the same as or different from each other.

[0252] In an exemplary embodiment of the present specification, R4 and R5 are the same as or different from each other, and are each independently an aromatic hydrocarbon ring or an aliphatic hydrocarbon ring, and bond with the adjacent R1 or R2 to form a five-membered ring or a six-membered ring.

[0253] In an exemplary embodiment of the present specification, R4 and R5 are the same as or different from each other, and are each independently a substituted or unsubstituted cycloalkyl group; or a group represented by the following formula 3-A, or bonded to an adjacent substituent to form a substituted or unsubstituted ring.

[0254] In an exemplary embodiment of the present specification, R4 and R5, while being a substituted or unsubstituted cycloalkyl group, bond with the adjacent R1 or R2 to form a substituted or unsubstituted ring.

[0255] In an exemplary embodiment of the present specification, R4 and R5 are the same as or different from each other, and are each independently a substituted or unsubstituted C3-C30 cycloalkyl group; or a group represented by the following formula 3-A, or are bonded to an adjacent substituent to form a substituted or unsubstituted C5-C30 hydrocarbon ring.

[0256] In an exemplary embodiment of the present specification, R4 and R5 are the same as or different from each other, and are each independently a substituted or unsubstituted cyclohexyl group; or a substituted or unsubstituted adamantyl group; or a group represented by the following formula 3-A, or bonded to an adjacent R1 or R2 to form a substituted or unsubstituted ring.

[0257] In an exemplary embodiment of the present specification, R4 and R5 are the same as or different from each other, and while each independently being an unsubstituted or methyl-substituted cyclohexyl group, bond with the adjacent R1 or R2 to form an unsubstituted or methyl-substituted ring.

[0258] In an exemplary embodiment of the present specification, R4 and R5 are the same as or different from each other, and while each independently being a group represented by the following Formula 3-A, bond with adjacent R1 or R2 to form an unsubstituted or R31-substituted ring.

[0259] In an exemplary embodiment of the present specification, R4 and R5 are groups represented by the following Formula 3-A.

[0260] [Formula 3-A]

[0261]

[0262] In Formula 3-A,

[0263] R31 is hydrogen; deuterium; cyano; halogen; substituted or unsubstituted alkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted silyl; substituted or unsubstituted aryl; substituted or unsubstituted heterocyclic; or substituted or unsubstituted amino, or bonds with an adjacent substituent to form a substituted or unsubstituted ring,

[0264] r31 is an integer of 0 to 5, and when r31 is 2 or more, R31 are the same as or different from each other, and

[0265] is the part connected to Formula 2,

[0266] In an exemplary embodiment of the present specification, when r31 is 2 or more, the plurality of R31s are the same as or different from each other.

[0267] In an exemplary embodiment of the present specification, R6, R7, and R31 are defined the same.

[0268] In an exemplary embodiment of the present specification, R31 may bond with an adjacent R1 or R2 to form a ring.

[0269] In an exemplary embodiment of the present specification, R31, R6, and R7 are connected to the ortho position relative to nitrogen (N) while being a substituent other than hydrogen. Specifically, in 3-A of the following structure, The position connected to the nitrogen (N) of Formula 2, in this regard, substituents other than hydrogen (R31, R6, and R7 halogen groups, cyano groups, alkyl groups, alkoxy groups, alkylthio groups, aryl groups, aryloxy groups, arylthio groups, heterocyclic groups, cycloalkyl groups, alkylsilyl groups, arylsilyl groups, arylalkyl groups, alkylamino groups, arylamino groups, heteroarylamino groups, etc.) are connected to one or both of the positions represented by the dotted line as the ortho position. In this case, a substituent may also be connected to the meta position or the para position relative to nitrogen (N) or a ring may be formed.

[0270]

[0271] In an exemplary embodiment of the present specification, R1 to R3, R6, R7 and R31 are the same as or different from each other, and are each 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 silyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthio group; or a substituted or unsubstituted amine group, or bonded to an adjacent substituent to form a substituted or unsubstituted ring.

[0272] In an exemplary embodiment of the present specification, R1 to R3, R6, R7 and R31 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1-C10 alkyl group; a substituted or unsubstituted C3-C30 cycloalkyl group; a substituted or unsubstituted C1-C30 alkylsilyl group; a substituted or unsubstituted C6-C60 arylsilyl group; a substituted or unsubstituted C6-C30 aryl group; a substituted or unsubstituted C2-C30 heterocyclyl group; a substituted or unsubstituted C1-C10 alkoxy group; a substituted or unsubstituted C6-C60 arylamine group; or a substituted or unsubstituted heteroarylamine group, or bonded to an adjacent substituent to form a substituted or unsubstituted C2-C30 ring.

[0273] In an exemplary embodiment of the present specification, R1 to R3, R6, R7 and R31 are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a C1-C10 alkyl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a C1-C10 alkyl group and a C6-C30 aryl group, or a substituent selected from two or more groups connected to each other; a C3-C30 cycloalkyl group; a C1-C30 alkylsilyl group; a C6-C60 arylsilyl group; C6-C30 aryl substituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen groups, cyano groups, C1-C10 alkyl groups, silyl groups, C1-C10 alkoxy groups, C6-C30 aryl groups and C9-C30 condensed ring groups, or substituents selected from two or more groups in the above groups connected; C6-C30 aryloxy groups; unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and C1-C10 alkyl groups, or substituents selected from two or more groups in the above groups connected C9-C30 fused hydrocarbon ring group; C2-C30 heterocyclic group which is unsubstituted or substituted by one or more substituents selected from the group consisting of deuterium, halogen groups, cyano groups, C1-C10 alkyl groups, silyl groups and C6-C30 aryl groups, or substituents connected to two or more groups selected from the above groups; C1-C10 alkoxy which is unsubstituted or substituted by a halogen group; or C2-C30 heterocyclic group which is unsubstituted or substituted by a halogen group; The amino group is substituted with one or more substituents selected from the group consisting of a C9-C30 condensed ring group, and a C2-C30 heterocyclic group, or with substituents selected from the above group connected to form a C2-C30 ring which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a cyano group, a halogen group, a C1-C10 alkyl group, a C1-C10 alkoxy group, a silyl group, and a C6-C30 aryl group, or with substituents selected from the above group connected to form a C2-C30 ring.

[0274] In an exemplary embodiment of the present specification, R1 to R3, R6, R7 and R31 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; an alkyl group which is unsubstituted or substituted with deuterium, a halogen group or a C6-C30 aryl group; a C3-C30 cycloalkyl group; a C1-C30 alkylsilyl group; a C6-C60 arylsilyl group; an alkyl group which is unsubstituted or substituted with deuterium, a halogen group, a cyano group, a C1-C10 alkyl group; , C1-C10 alkyl substituted with deuterium, C1-C10 haloalkyl, C1-C10 alkoxy, C1-C10 haloalkoxy, C9-C30 fused hydrocarbon ring group, C9-C30 fused hydrocarbon ring group substituted with C1-C10 alkyl, or C6-C30 aryl substituted with C1-C30 alkylsilyl; C6-C30 aryloxy; unsubstituted or substituted with deuterium, C1-C10 alkyl, C1-C10 alkoxy, C1-C10 haloalkoxy, C9-C30 fused hydrocarbon ring group, C9-C30 fused hydrocarbon ring group substituted with C1-C10 alkyl, or C6-C30 aryl substituted with C1-C30 alkylsilyl C2-C30 heterocyclyl, C1-C30 alkylsilyl, C6-C30 aryl, C6-C30 aryl substituted with deuterium, or C2-C30 heterocyclyl substituted with C1-C30 alkylsilyl; C1-C10 alkoxy, unsubstituted or substituted with a halogen group; or C1-C10 alkyl, C1-C10 alkyl, C1-C30 alkylsilyl, C6-C30 arylsilyl, C2-C30 heterocyclyl, C1-C30 alkylsilyl, C6-C30 arylsilyl, C2-C30 heterocyclyl, C1-C30 alkylsilyl, C6-C30 arylsilyl, C2-C30 heterocyclyl, C1-C30 alkylsilyl, C1-C30 alkylsilyl, C6-C30 arylsilyl, C2-C30 heterocyclyl, C1-C30 alkylsilyl, C1-C30 alkylsilyl, C2 ... The present invention relates to a heterocyclic group which is substituted with a C7-C30 alkyl group, a C6-C60 arylamine group which is substituted with a C5-C30 aliphatic hydrocarbon ring and is not fused or is fused with a C5-C30 aliphatic hydrocarbon ring, or is bonded to an adjacent substituent to form a C2-C30 ring which is unsubstituted or substituted with deuterium, a C1-C10 alkyl group, a C1-C10 alkyl group substituted with deuterium, a C6-C30 aryl group, a C6-C30 aryl group substituted with deuterium, or a C1-C30 alkylsilyl group.

[0275] In an exemplary embodiment of the present specification, R1 to R3, R6, R7 and R31 are the same as or different from each other, and are each independently hydrogen; deuterium; fluoro; cyano; unsubstituted or deuterium-substituted methyl; ethyl; unsubstituted or deuterium-substituted isopropyl; unsubstituted or deuterium-substituted tert-butyl; isopropyl substituted with phenyl and deuterium; cyclohexyl; adamantyl; trimethylsilyl; triphenylsilyl; unsubstituted or deuterium-substituted, fluoro, cyano, methyl, isopropyl, tert-butyl, CD3, C(CD3 )3, CF3, trimethylsilyl, tert-butyldimethylsilyl, tetramethyltetrahydronaphthyl, dimethyldihydroindenyl, or tetramethyldihydroindenyl substituted phenyl; unsubstituted or substituted biphenyl with deuterium, fluoro, cyano, methyl, isopropyl, tert-butyl, CD3, CF3, C(CD3)3, trimethylsilyl, tert-butyldimethylsilyl, tetramethyltetrahydronaphthyl, dimethyldihydroindenyl, or tetramethyldihydroindenyl; naphthyl; phenanthrenyl; unsubstituted or substituted fluorenyl with methyl or phenyl; unsubstituted unsubstituted or substituted with methyl or phenyl benzofluorenyl; unsubstituted or substituted with methyl hydronaphthyl; unsubstituted or substituted with methyl dihydroindanyl; unsubstituted or substituted with methyl phenylamino; unsubstituted or substituted with deuterium, methyl, isopropyl, tert-butyl, CD3, C(CD3)3, isopropyl substituted with phenyl, trimethylsilyl, tert-butyldimethylsilyl, triphenylsilyl, phenyl, biphenyl, dimethylfluorenyl, dibenzofuranyl, or dibenzothiophenyl and unfused or fused with a cyclopentene ring or a cyclohexene ring; unsubstituted a methoxy group which is substituted or substituted with a fluoro group; a dibenzofuranyl group which is unsubstituted or substituted with a methyl group, a tert-butyl group or a phenyl group; a naphthobenzofuranyl group; a dibenzothienyl group which is unsubstituted or substituted with a methyl group, a tert-butyl group or a phenyl group; a naphthobenzothienyl group; a dibenzothiolar group which is unsubstituted or substituted with a methyl group or a phenyl group; a naphthobenzothiolar group which is unsubstituted or substituted with a methyl group or a phenyl group; a pyridyl group which is unsubstituted or substituted with a deuterium group, a methyl group, an isopropyl group or a tert-butyl group; and a group represented by one of the following formulae 2-A-1 to 2-A-6.

[0276] In an exemplary embodiment of the present specification, R1 to R3, R6, R7, and R31 are bonded to adjacent substituents to form a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic hydrocarbon ring; a substituted or unsubstituted aromatic heterocycle; or a substituted or unsubstituted aliphatic heterocycle.

[0277] In an exemplary embodiment of the present specification, R1 is bonded to an adjacent R1 to form a substituted or unsubstituted ring. In another exemplary embodiment, R2 is bonded to an adjacent R2 to form a substituted or unsubstituted ring. In yet another exemplary embodiment, R3 is bonded to an adjacent R3 to form a substituted or unsubstituted ring. In yet another exemplary embodiment, R6 is bonded to an adjacent R6 to form a substituted or unsubstituted ring. In yet another exemplary embodiment, R7 is bonded to an adjacent R7 to form a substituted or unsubstituted ring. In yet another exemplary embodiment, R31 is bonded to an adjacent R31 to form a substituted or unsubstituted ring.

[0278] The "aliphatic hydrocarbon ring formed by bonding two adjacent R1, two adjacent R2, two adjacent R3, two adjacent R6, two adjacent R7, or two adjacent R31 to each other" may be a C5-C20 aliphatic hydrocarbon ring. Specifically, the ring may be a cyclohexene ring; a cyclopentene ring; a bicyclo[2.2.1]heptene ring; or a bicyclo[2.2.2]octene ring, and the ring may be unsubstituted or substituted with a methyl group.

[0279] In addition, the "aromatic hydrocarbon ring formed by bonding two adjacent R1, two adjacent R2, two adjacent R3, two adjacent R6, two adjacent R7, or two adjacent R31 to each other" may be a C6-C20 aromatic hydrocarbon ring. Specifically, the ring may be an indene ring; or a spiro[indene-fluorene] ring, and the ring may be unsubstituted or substituted with a methyl group, an isopropyl group, a tert-butyl group, or a phenyl group.

[0280] Furthermore, the “aromatic heterocyclic ring formed by bonding two adjacent R1, two adjacent R2, two adjacent R3, two adjacent R6, two adjacent R7, or two adjacent R31 to each other” may be a C5-C20 aromatic heterocyclic ring containing one or more of O, S, Si, and N. Specifically, the aromatic heterocyclic ring may be a furan ring; a dihydrofuran ring; a benzofuran ring; a naphthofuran ring; a thiophene ring; a dihydrothiophene ring; a benzothiophene ring; a naphthofuran ring; an indole ring; a benzindole ring; a silole ring; a benzosilole ring; or a naphthosilole ring, and the ring is unsubstituted or substituted with a methyl group, an isopropyl group, a tert-butyl group, or a phenyl group.

[0281] In an exemplary embodiment of the present specification, two adjacent R1, two adjacent R2, two adjacent R3, two adjacent R6, two adjacent R7, or two adjacent R31 are bonded to each other to form a ring among Cy1 to Cy4 to be described below.

[0282] In an exemplary embodiment of the present specification, Formula 201 is any one of the following (1) to (3).

[0283] (1) at least one of R1 to R3, R6, and R7 is a substituted or unsubstituted cycloalkyl group; or a group represented by the following formula 2-A; or

[0284] (2) at least one of R1 to R3, R6, and R7 is a group represented by the following formula 2-B; or

[0285] (3) two adjacent R1, two adjacent R2, two adjacent R3, two adjacent R6 or two adjacent R7 are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring,

[0286]

[0287] In Formula 2-A and Formula 2-B,

[0288] T11 to T19 and A11 to A14 are the same as or different from each other, and are each 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 silyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthio group; or a substituted or unsubstituted amino group, or bond with an adjacent substituent to form a substituted or unsubstituted ring,

[0289] L11 is a direct bond; or a substituted or unsubstituted arylene group,

[0290] p1 is 0 or 1,

[0291] Y1 is C or Si,

[0292] At least one of T17 to T19 is a substituted or unsubstituted aryl group; and

[0293] * indicates the bonding position to Formula 201.

[0294] In this specification, the fact that equation 201 is any one of (1) to (3) includes not only the case where equation 201 corresponds to one of (1) to (3), but also the case where equation 201 corresponds to two or three of (1) to (3).

[0295] In an exemplary embodiment of the present specification, one or more of R1 to R3, R6, and R7 are represented by Formula 2-A or 2-B.

[0296] In an exemplary embodiment of the present specification, two adjacent R1, two adjacent R2, two adjacent R3, two adjacent R6 or two adjacent R7 are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring. Specifically, two adjacent R1, two adjacent R2, two adjacent R3, two adjacent R6 or two adjacent R7 are bonded to each other to form the following ring Cy1 to be described below. In this case, one of the rings formed by bonding R1 to R7 with adjacent substituents may be an aliphatic hydrocarbon ring, and the case of further forming an aromatic hydrocarbon ring, an aromatic heterocycle or an aliphatic heterocycle is not excluded.

[0297] In an exemplary embodiment of the present specification, T17 to T19 are the same as or different from each other and are each independently a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, and at least one of T17 to T19 is a substituted or unsubstituted aryl group.

[0298] In an exemplary embodiment of the present specification, T17 to T19 are the same as or different from each other and are each independently a substituted or unsubstituted C1-C10 alkyl group; or a substituted or unsubstituted C6-C30 aryl group, and at least one of T17 to T19 is a substituted or unsubstituted C6-C30 aryl group.

[0299] In an exemplary embodiment of the present specification, T17 to T19 are the same as or different from each other, and are each independently an unsubstituted or deuterium-substituted C1-C6 alkyl group; or an unsubstituted or deuterium-substituted C6-C20 aryl group, and at least one of T17 to T19 is an unsubstituted or deuterium-substituted C6-C20 aryl group.

[0300] In an exemplary embodiment of the present specification, one of T17 to T19 is an unsubstituted or deuterium-substituted C6-C20 aryl group, and two of T17 to T19 are an unsubstituted or deuterium-substituted C1-C6 alkyl group.

[0301] In an exemplary embodiment of the present specification, T17 to T19 are the same as or different from each other and are each independently a C1-C6 alkyl group; or a C6-C20 aryl group, and at least one of T17 to T19 is a C6-C20 aryl group.

[0302] In an exemplary embodiment of the present specification, T17 is a substituted or unsubstituted aryl group, T18 is a substituted or unsubstituted alkyl group, and T19 is a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.

[0303] In an exemplary embodiment of the present specification, T17 to T19 are the same as or different from each other and are each independently an unsubstituted or deuterium-substituted methyl group; or an unsubstituted or deuterium-substituted phenyl group, and at least one of T17 to T19 is an unsubstituted or deuterium-substituted phenyl group.

[0304] In an exemplary embodiment of the present specification, one of T17 to T19 is an unsubstituted or deuterium-substituted phenyl group, and two of T17 to T19 are an unsubstituted or deuterium-substituted methyl group.

[0305] In an exemplary embodiment of the present specification, T17 to T19 are the same as or different from each other and are each independently a methyl group; or a phenyl group, and at least one of T17 to T19 is a phenyl group.

[0306] In an exemplary embodiment of the present specification, one of T17 to T19 is a phenyl group, and the remaining two are methyl groups.

[0307] In an exemplary embodiment of the present specification, Formula 2-A is represented by one of Formulae 2-A-1 to 2-A-6 to be described below.

[0308] In an exemplary embodiment of the present specification, a ring formed by bonding two adjacent R1, two adjacent R2, two adjacent R3, or two adjacent R6 to each other is one of the following rings Cy1 to Cy4.

[0309]

[0310] In Cy1 to Cy4,

[0311] * is the carbon participating in the ring formation in R1 to R3, R6 and R7,

[0312] Y10 is O; S; Si(Ra3)(Ra4); or N(Ra5),

[0313] Y11 is O; S; Si(Ra3)(Ra4); C(Ra3)(Ra4); or N(Ra5).

[0314] R41 to R44 and Ra3 to Ra5 ​​are the same as or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, and bond with an adjacent substituent to form a substituted or unsubstituted ring,

[0315] p6 is an integer from 1 to 3, and

[0316] R41 is an integer from 0 to 10, R42 is an integer from 0 to 4, R43 is an integer from 0 to 2, R44 is an integer from 0 to 4, and when R41 to R44 are each 2 or more, the substituents in brackets are the same as or different from each other.

[0317] In an exemplary embodiment of the present specification, when r41 is 2 or more, a plurality of R41 are the same or different from each other. In another exemplary embodiment, when r42 is 2 or more, a plurality of R42 are the same or different from each other. In another exemplary embodiment, when r43 is 2 or more, a plurality of R43 are the same or different from each other. In yet another exemplary embodiment, when r44 is 2 or more, a plurality of R44 are the same or different from each other.

[0318] In the structure, * is the position where the substituent is fused to Formula 2.

[0319] In an exemplary embodiment of the present specification, p6 is 1 or 2.

[0320] In an exemplary embodiment of the present specification, R41 to R43 and Ra3 to Ra5 ​​are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted C1-C10 alkyl group; a substituted or unsubstituted C6-C30 aryl group, or bonded to an adjacent substituent to form a substituted or unsubstituted ring.

[0321] In an exemplary embodiment of the present specification, R41 to R43 and Ra3 to Ra5 ​​are the same as or different from each other, and are each independently hydrogen; deuterium; a C1-C6 alkyl group which is unsubstituted or substituted with deuterium; or a C6-C20 aryl group which is unsubstituted or substituted with deuterium or a C1-C6 alkyl group, and bonds with an adjacent substituent to form a C5-C20 hydrocarbon ring which is unsubstituted or substituted with deuterium, a C1-C6 alkyl group or a C6-C20 aryl group; or a C2-C20 heterocyclic ring which is unsubstituted or substituted with deuterium, a C1-C6 alkyl group or a C6-C20 aryl group.

[0322] In an exemplary embodiment of the present specification, R41 to R43 are the same as or different from each other, and are each independently hydrogen; deuterium; an unsubstituted or deuterium-substituted methyl group; an isopropyl group; a tert-butyl group; or a phenyl group.

[0323] In an exemplary embodiment of the present specification, R41 and R41 are bonded to obtain a form in which the Cy1 ring is a bicyclic ring (a bicyclic alkyl ring or a bicyclic olefin ring), such as a bridged ring or a condensed ring. Specifically, Cy1 is a bicyclo [2.2.2] octene ring; or a bicyclo [2.2.1] heptene ring, and the ring is unsubstituted or substituted by R41.

[0324] In an exemplary embodiment of the present specification, R42 bonds with adjacent R42 to form a substituted or unsubstituted aliphatic hydrocarbon ring.

[0325] In an exemplary embodiment of the present specification, R42 bonds to adjacent R42 to form a C5-C30 aliphatic hydrocarbon ring which is unsubstituted or substituted with deuterium, a C1-C10 alkyl group, or a C1-C10 alkyl group substituted with deuterium.

[0326] In an exemplary embodiment of the present specification, R42 bonds to an adjacent R42 to form a C5-C20 aliphatic hydrocarbon ring which is unsubstituted or substituted with deuterium, a C1-C6 alkyl group, or a C1-C6 alkyl group substituted with deuterium.

[0327] In an exemplary embodiment of the present specification, R43 is bonded to an adjacent R43 to form a substituted or unsubstituted C5-C30 aromatic hydrocarbon ring; a substituted or unsubstituted C5-C30 aliphatic hydrocarbon ring; a substituted or unsubstituted C2-C30 aromatic heterocyclic ring; or a substituted or unsubstituted C2-C30 aliphatic hydrocarbon ring.

[0328] In an exemplary embodiment of the present specification, R43 is bonded to an adjacent R43 to form an indene ring; a benzene ring; a naphthalene ring; a cyclopentene ring; a cyclohexene ring; a tetralin ring; a bicyclo[2.2.2]octene ring; a bicyclo[2.2.1]heptene ring; a benzofuran ring; a benzothiophene ring; a benzosilole ring; or an indole ring, and the ring is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a C1-C6 alkyl group, and a C6-C20 aryl group, or substituents in which two or more groups selected from the above group are connected.

[0329] In an exemplary embodiment of the present specification, the above-mentioned definitions of R1 to R3 and R31 may be applied to R44.

[0330] In an exemplary embodiment of the present specification, R44 bonds with adjacent R44 to form a substituted or unsubstituted hydrocarbon ring.

[0331] In an exemplary embodiment of the present specification, R44 bonds with adjacent R44 to form a benzene ring which is unsubstituted or substituted with R1 to R3.

[0332] In an exemplary embodiment of the present specification, Ra3 to Ra5 ​​are the same as or different from each other, and are each independently a substituted or unsubstituted C1-C10 alkyl group; a substituted or unsubstituted C6-C30 aryl group, or bonded with an adjacent substituent to form a substituted or unsubstituted C5-C30 hydrocarbon ring.

[0333] In an exemplary embodiment of the present specification, Ra3 and Ra4 are the same as or different from each other, and are each independently a C1-C6 alkyl group that is unsubstituted or substituted with deuterium; a C6-C20 aryl group that is unsubstituted or substituted with deuterium or a C1-C6 alkyl group, or is bonded to an adjacent substituent to form a C5-C20 hydrocarbon ring that is unsubstituted or substituted with deuterium or a C1-C6 alkyl group.

[0334] In an exemplary embodiment of the present specification, Ra3 and Ra4 are the same as or different from each other, and are each independently a methyl group; or a phenyl group, or are bonded to each other to form a fluorene ring which is unsubstituted or substituted with a methyl group, an isopropyl group, or a tert-butyl group.

[0335] In an exemplary embodiment of the present specification, Ra5 is a C6-C30 aryl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a C1-C10 alkyl group and a C1-C10 alkoxy group, or a substituent in which two or more groups selected from the above group are connected.

[0336] In an exemplary embodiment of the present specification, Ra5 is a C6-C20 aryl group which is unsubstituted or substituted with deuterium, a halogen group, a C1-C6 alkyl group, a C1-C6 alkyl group substituted with deuterium, a C1-C6 haloalkyl group, or a C1-C6 haloalkoxy group.

[0337] In an exemplary embodiment of the present specification, Ra5 is a phenyl group which is unsubstituted or substituted with deuterium, a methyl group, a methyl group substituted with deuterium, a trifluoromethyl group, a trifluoromethoxy group, an isopropyl group or a tert-butyl group; a biphenyl group; or a terphenyl group.

[0338] In an exemplary embodiment of the present specification, Y10 is O; S; Si(Ra3)(Ra4); or N(Ra5).

[0339] In an exemplary embodiment of the present specification, an aliphatic hydrocarbon ring formed by bonding two adjacent R1, two adjacent R2, two adjacent R3, two adjacent R6, or two adjacent R7 to each other is Cy1.

[0340] In an exemplary embodiment of the present specification, Cy1 is one selected from the following structures.

[0341]

[0342] In an exemplary embodiment of the present specification, Cy2 is one selected from the following structures, and Y10, R42, and r42 are the same as those described above.

[0343]

[0344] In the structure, p7 is 1 to 3, r421 is an integer of 0 to 10, and when r421 is 2 or more, R42 are the same as or different from each other.

[0345] In an exemplary embodiment of the present specification, Cy3 is one selected from the following structures.

[0346]

[0347] In the structure,

[0348] Y11 is the same as that described above.

[0349] R431 is hydrogen; deuterium; substituted or unsubstituted alkyl; or substituted or unsubstituted aryl,

[0350] r431 is an integer from 0 to 2, r432 is an integer from 0 to 4, and r433 is an integer from 0 to 6, and

[0351] When r431 is 2 or r432 and r433 are 2 or more, R431 are the same as or different from each other.

[0352] In an exemplary embodiment of the present specification, R431 is the same as in the definition of R43 described above, except that R431 forms a ring.

[0353] In an exemplary embodiment of the present specification, R43 is hydrogen; deuterium; methyl; isopropyl; tert-butyl; or phenyl.

[0354] In an exemplary embodiment of the present specification, the heterocyclic group of R1 to R3 and R6 includes one or more of N, O, S, and Si as a hetero atom.

[0355] In an exemplary embodiment of the present specification, the O-containing heterocyclic group of R1 to R3 and R6 may be a benzofuranyl group; a dibenzofuranyl group; or a naphthobenzofuranyl group, and is unsubstituted or substituted with deuterium, a C1-C6 alkyl group, or a C6-C20 aryl group.

[0356] In an exemplary embodiment of the present specification, the S-containing heterocyclic group of R1 to R3 and R6 may be a benzothienyl group; a dibenzothienyl group; or a naphthobenzothienyl group, and is unsubstituted or substituted with deuterium, a C1-C6 alkyl group, or a C6-C20 aryl group.

[0357] In an exemplary embodiment of the present specification, the Si-containing heterocyclic group of R1 to R3 and R6 may be a benzothirolyl group; a dibenzothirolyl group; or a naphthobenzothirolyl group, and is unsubstituted or substituted with deuterium, a C1-C6 alkyl group, or a C6-C20 aryl group.

[0358] In an exemplary embodiment of the present specification, the N-containing heterocyclic group of R1 to R3 and R6 is represented by a substituted or unsubstituted pyridyl group; or is represented by one of the following Formulae 2-A-1 to 2-A-6.

[0359]

[0360] In Formula 2-A-1 to Formula 2-A-6,

[0361] * is the part connected to Formula 2,

[0362] Y1 is C or Si,

[0363] p1 is 0 or 1,

[0364] Y6 and Y7 are the same as or different from each other and are each independently O; S; C(T26)(T27); or Si(T26)(T27),

[0365] T11 to T16 and T20 to T29 are the same as or different from each other, and are each 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 silyl group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthio group; or a substituted or unsubstituted amino group, or bond with an adjacent substituent to form a substituted or unsubstituted ring,

[0366] Cy5 is an aliphatic hydrocarbon ring,

[0367] Cy6 is an aromatic hydrocarbon ring, and

[0368] t28 is an integer of 0 to 10, t29 is an integer of 0 to 10, and when t28 and t29 are each 2 or more, the substituents in the brackets are the same as or different from each other.

[0369] In an exemplary embodiment of the present specification, Y6 is O; or S.

[0370] In an exemplary embodiment of the present specification, Y6 is C(T26)(T27); or Si(T26)(T27).

[0371] In an exemplary embodiment of the present specification, Y6 is C(T26)(T27).

[0372] In an exemplary embodiment of the present specification, Y7 are the same as or different from each other, and are each independently O; S; or C(T26)(T27).

[0373] In an exemplary embodiment of the present specification, t28 is an integer of 0 to 6, and when t28 is 2 or more, a plurality of T28 are the same as or different from each other.

[0374] In an exemplary embodiment of the present specification, t29 is an integer of 0 to 10, and when t29 is 2 or more, a plurality of T29 are the same as or different from each other.

[0375] In an exemplary embodiment of the present specification, T11 to T14 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted alkylsilyl group; or a substituted or unsubstituted arylsilyl group, or bond with an adjacent substituent to form a ring.

[0376] In an exemplary embodiment of the present specification, T11 to T14 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1-C10 alkyl group; a substituted or unsubstituted C6-C30 aryl group; a substituted or unsubstituted C1-C30 alkylsilyl group; or a substituted or unsubstituted C6-C60 arylsilyl group, or are bonded to an adjacent substituent to form a substituted or unsubstituted C6-C30 aromatic hydrocarbon ring.

[0377] In an exemplary embodiment of the present specification, T11 to T14 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; a C1-C6 alkyl group which is unsubstituted or substituted with deuterium; a C6-C20 aryl group which is unsubstituted or substituted with deuterium or a C1-C6 alkyl group; or a C1-C30 alkylsilyl group, or are bonded to an adjacent substituent to form a C6-C30 aromatic hydrocarbon ring which is unsubstituted or substituted with deuterium or a C1-C6 alkyl group.

[0378] In an exemplary embodiment of the present specification, T11 to T14 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a cyano group; a methyl group that is unsubstituted or substituted with deuterium; an isopropyl group; a tert-butyl group; a phenyl group that is unsubstituted or substituted with deuterium, a methyl group, an isopropyl group, or a tert-butyl group; or a trimethylsilyl group, or is bonded to an adjacent substituent to form a benzene ring that is unsubstituted or substituted with deuterium, a methyl group, an isopropyl group, or a tert-butyl group.

[0379] In an exemplary embodiment of the present specification, T15 and T16 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, or bond to each other to form a substituted or unsubstituted hydrocarbon ring.

[0380] In an exemplary embodiment of the present specification, T15 and T16 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted C1-C6 alkyl group; or a substituted or unsubstituted C6-C20 aryl group, or are bonded to each other to form a substituted or unsubstituted C5-C20 hydrocarbon ring.

[0381] In an exemplary embodiment of the present specification, T15 and T16 are the same as or different from each other and are each independently hydrogen; deuterium; or methyl, or are bonded to each other to form a fluorene ring while being an unsubstituted or tert-butyl-substituted phenyl group; or an unsubstituted or tert-butyl-substituted dibenzosilole ring.

[0382] In an exemplary embodiment of the present specification, Y1 is C.

[0383] In an exemplary embodiment of the present specification, Y1 is Si.

[0384] In an exemplary embodiment of the present specification, when p1 is 0, the site including Y1 is a direct bond.

[0385] In an exemplary embodiment of the present specification, T20 to T27 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted C1-C10 alkyl group; a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C1-C30 alkylsilyl group.

[0386] In an exemplary embodiment of the present specification, T20 to T27 are the same as or different from each other, and are each independently hydrogen; deuterium; an unsubstituted or deuterium-substituted C1-C6 alkyl group; an unsubstituted or deuterium-substituted C6-C20 aryl group; or a substituted or unsubstituted C1-C18 alkylsilyl group.

[0387] In an exemplary embodiment of the present specification, T20 to T27 are the same as or different from each other, and are each independently hydrogen; deuterium; methyl; phenyl; or trimethylsilyl.

[0388] In an exemplary embodiment of the present specification, T26 and T27 are each a methyl group.

[0389] In an exemplary embodiment of the present specification, T20 to T27 are each a methyl group.

[0390] In an exemplary embodiment of the present specification, T28 and T29 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted C1-C6 alkyl group; or a substituted or unsubstituted C6-C20 aryl group.

[0391] In an exemplary embodiment of the present specification, T28 and T29 are the same as or different from each other, and are each independently hydrogen; deuterium; an unsubstituted or deuterium-substituted C1-C6 alkyl group; or an unsubstituted or deuterium-substituted C6-C20 aryl group.

[0392] In an exemplary embodiment of the present specification, T28 and T29 are the same as or different from each other, and are each independently hydrogen; deuterium; tert-butyl group; or phenyl group.

[0393] In an exemplary embodiment of the present specification, T28 and T29 are the same as or different from each other, and are each independently hydrogen; deuterium; or a tert-butyl group.

[0394] In an exemplary embodiment of the present specification, T29 is optionally bonded with an adjacent T29 to form a substituted or unsubstituted aromatic hydrocarbon ring.

[0395] In an exemplary embodiment of the present specification, T29 is bonded to an adjacent T29 to form a benzene ring.

[0396] In an exemplary embodiment of the present specification, T28 is hydrogen; deuterium; tert-butyl; or a phenyl group.

[0397] In an exemplary embodiment of the present specification, T28 is hydrogen; deuterium; or a tert-butyl group.

[0398] In an exemplary embodiment of the present specification, T28 is hydrogen; or deuterium.

[0399] In an exemplary embodiment of the present specification, T29 is hydrogen; or deuterium.

[0400] In an exemplary embodiment of the present specification, Cy5 is a C5-C20 aliphatic hydrocarbon ring.

[0401] In an exemplary embodiment of the present specification, Cy5 is a cyclopentane ring; a cyclohexane ring; or a cycloheptane ring.

[0402] In an exemplary embodiment of the present specification, Cy5 is a cyclohexane ring.

[0403] In an exemplary embodiment of the present specification, Cy6 is a C6-C20 aromatic hydrocarbon ring.

[0404] In an exemplary embodiment of the present specification, Cy6 is a benzene ring; or a naphthalene ring.

[0405] In an exemplary embodiment of the present specification, Cy6 is a benzene ring.

[0406] In an exemplary embodiment of the present specification, T17 to T19 are the same as or different from each other and are each independently a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, and at least one of T17 to T19 is a substituted or unsubstituted aryl group.

[0407] In an exemplary embodiment of the present specification, T17 to T19 are the same as or different from each other and are each independently a substituted or unsubstituted C1-C10 alkyl group; or a substituted or unsubstituted C6-C30 aryl group, and at least one of T17 to T19 is a substituted or unsubstituted C6-C30 aryl group.

[0408] In an exemplary embodiment of the present specification, T17 to T19 are the same as or different from each other, and are each independently an unsubstituted or deuterium-substituted C1-C6 alkyl group; or an unsubstituted or deuterium-substituted C6-C20 aryl group, and at least one of T17 to T19 is an unsubstituted or deuterium-substituted C6-C20 aryl group.

[0409] In an exemplary embodiment of the present specification, one of T17 to T19 is an unsubstituted or deuterium-substituted C6-C20 aryl group, and two of T17 to T19 are an unsubstituted or deuterium-substituted C1-C6 alkyl group.

[0410] In an exemplary embodiment of the present specification, T17 to T19 are the same as or different from each other and are each independently a C1-C6 alkyl group; or a C6-C20 aryl group, and at least one of T17 to T19 is a C6-C20 aryl group.

[0411] In an exemplary embodiment of the present specification, T17 is a substituted or unsubstituted aryl group, T18 is a substituted or unsubstituted alkyl group, and T19 is a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.

[0412] In an exemplary embodiment of the present application, T17 to T19 are the same as or different from each other and are each independently an unsubstituted or deuterium-substituted methyl group; or an unsubstituted or deuterium-substituted phenyl group, and at least one of T17 to T19 is an unsubstituted or deuterium-substituted phenyl group.

[0413] In an exemplary embodiment of the present specification, one of T17 to T19 is an unsubstituted or deuterium-substituted phenyl group, and two of T17 to T19 are an unsubstituted or deuterium-substituted methyl group.

[0414] In an exemplary embodiment of the present specification, T17 to T19 are the same as or different from each other and are each independently a methyl group; or a phenyl group, and at least one of T17 to T19 is a phenyl group.

[0415] In an exemplary embodiment of the present specification, one of T17 to T19 is a phenyl group, and the other two are methyl groups.

[0416] In an exemplary embodiment of the present specification, Formula 202 is represented by the following Formula 202-1 or Formula 202-2.

[0417] [Formula 202-1]

[0418]

[0419] [Formula 202-2]

[0420]

[0421] In Formula 202-1 and Formula 202-2, definitions of R1 to R3, R6, Y2, Z1, Z2, A21 to A24, r1, r2′, r3, and r6 are the same as those defined in Formula 202.

[0422] In an exemplary embodiment of the present specification, Formula 203 is represented by one of the following Formulas 203-1 to 203-3.

[0423] [Formula 203-1]

[0424]

[0425] [Formula 203-2]

[0426]

[0427] [Formula 203-3]

[0428]

[0429] In Formula 203-1 and Formula 203-3, definitions of R1 to R3, Y3, Y4, Z3 to Z6, A25 to A32, r1′, r2′, and r3 are the same as those defined in Formula 203.

[0430] In an exemplary embodiment of the present specification, Z1 to Z6 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, and bond with an adjacent substituent to form a substituted or unsubstituted ring.

[0431] In an exemplary embodiment of the present specification, Z1 to Z6 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted C1-C10 alkyl group; or a substituted or unsubstituted C6-C30 aryl group, and bond with an adjacent substituent to form a substituted or unsubstituted C5-C30 ring.

[0432] In an exemplary embodiment of the present specification, Z1 to Z6 are the same as or different from each other, and are each independently hydrogen; deuterium; C1-C6 alkyl which is unsubstituted or substituted with deuterium; or C6-C20 aryl which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and C1-C6 alkyl or substituents in which two or more groups are connected selected from the above group, and a C5-C20 ring which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and C1-C6 alkyl or substituents in which two or more groups are connected selected from the above group, and is bonded to an adjacent substituent to form a C5-C20 ring.

[0433] In an exemplary embodiment of the present specification, Z1 to Z6 are the same as or different from each other, and are each independently hydrogen; deuterium; unsubstituted or deuterium-substituted C1-C6 alkyl; or unsubstituted or deuterium-substituted C6-C20 aryl, and bonded to an adjacent substituent to form a three-membered ring that is unsubstituted or substituted with deuterium, C1-C6 alkyl, or deuterium-substituted C1-C6 alkyl.

[0434] The fact that Z1 to Z6 bond to adjacent substituents means that Z1 and Z2; Z3 and Z4; or Z5 and Z6 bond to each other.

[0435] In an exemplary embodiment of the present specification, the ring formed by bonding Z1 to Z6 to adjacent substituents is a fluorene ring, a dibenzosilole ring, or a xanthene ring. Specifically, two adjacent substituents are directly bonded to each other while being phenyl to form a fluorene ring or a dibenzosilole ring, or are bonded via -O- to form a xanthene ring while being phenyl. In this case, the ring may be substituted with deuterium, methyl, isopropyl, tert-butyl or phenyl.

[0436] In an exemplary embodiment of the present specification, Z1 to Z6 are the same as or different from each other, and are each independently a substituted or unsubstituted methyl group; or a substituted or unsubstituted phenyl group; or

[0437] While each of them is a substituted or unsubstituted phenyl group, Z1 and Z2, Z3 and Z4, or Z5 and Z6 are directly bonded to each other to form a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted dibenzosilole ring; or while being a substituted or unsubstituted phenyl group, they are bonded via -O- to form a substituted or unsubstituted xanthene ring.

[0438] In an exemplary embodiment of the present specification, A21 to A32 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, or bond with an adjacent substituent to form a substituted or unsubstituted hydrocarbon ring.

[0439] In an exemplary embodiment of the present specification, A21 to A32 are the same as or different from each other, and are each independently a substituted or unsubstituted C1-C6 alkyl group; or a substituted or unsubstituted C6-C20 aryl group, or are bonded with an adjacent substituent to form a substituted or unsubstituted C5-C20 aliphatic hydrocarbon ring; or a substituted or unsubstituted C6-C20 aromatic hydrocarbon ring.

[0440] In an exemplary embodiment of the present specification, A21 to A32 are the same as or different from each other, and are each independently a C1-C6 alkyl group which is unsubstituted or substituted with deuterium; or a C6-C20 aryl group which is unsubstituted or substituted with deuterium, a C1-C6 alkyl group, or a C1-C6 alkyl group which is substituted with deuterium, or is bonded with an adjacent substituent to form a C5-C20 aliphatic hydrocarbon ring which is unsubstituted or substituted with deuterium, a C1-C6 alkyl group, or a C1-C6 alkyl group which is substituted with deuterium; or a C6-C10 aromatic hydrocarbon ring which is unsubstituted or substituted with deuterium, a C1-C6 alkyl group, or a C1-C6 alkyl group which is substituted with deuterium.

[0441] The fact that A21 to A32 are bonded to the adjacent substituent to form a ring means that two of A21 to A24 are bonded to form an aliphatic hydrocarbon ring; two of A25 to A28 are bonded to form an aliphatic hydrocarbon ring; two of A29 to A32 are bonded to form an aliphatic hydrocarbon ring; A21 to A24 are bonded to each other to form an aromatic hydrocarbon ring; A25 to A28 are bonded to each other to form an aromatic hydrocarbon ring; or A29 to A32 are bonded to each other to form an aromatic hydrocarbon ring.

[0442] In an exemplary embodiment of the present specification, i) two of A21 to A24 are bonded to each other to form a substituted or unsubstituted C5-C10 aliphatic hydrocarbon ring, and the remaining two are hydrogen; deuterium; a substituted or unsubstituted C1-C6 alkyl group; or a substituted or unsubstituted C6-C20 aryl group, or ii) A21 to A24 are bonded to each other to form a substituted or unsubstituted C6-C10 aromatic hydrocarbon ring.

[0443] In an exemplary embodiment of the present specification, i) two of A21 to A24 are bonded to each other to form a substituted or unsubstituted C5-C10 aliphatic hydrocarbon ring, and the remaining two are hydrogen; deuterium; an unsubstituted or deuterium-substituted C1-C6 alkyl group; or an unsubstituted or deuterium-substituted C6-C20 aryl group, or ii) A21 to A24 are bonded to each other to form an unsubstituted or deuterium-substituted C6-C10 aromatic hydrocarbon ring, C1-C6 alkyl group, or a deuterium-substituted C1-C6 alkyl group.

[0444] In an exemplary embodiment of the present specification, i) two of A21 to A24 are bonded to each other to form a cyclohexane ring, and the remaining two are hydrogen; deuterium; unsubstituted or deuterium-substituted methyl; or unsubstituted or deuterium-substituted phenyl, or ii) A21 to A24 are bonded to each other to form a benzene ring that is unsubstituted or substituted with deuterium, methyl, tert-butyl, methyl substituted with deuterium, or tert-butyl substituted with deuterium; or an indene ring that is unsubstituted or substituted with methyl or tert-butyl.

[0445] In an exemplary embodiment of the present specification, i) two of A25 to A28 are bonded to each other to form a substituted or unsubstituted C5-C10 aliphatic hydrocarbon ring, and the remaining two are hydrogen; deuterium; a substituted or unsubstituted C1-C6 alkyl group; or a substituted or unsubstituted C6-C20 aryl group, or ii) A25 to A28 are bonded to each other to form a substituted or unsubstituted C6-C10 aromatic hydrocarbon ring.

[0446] In an exemplary embodiment of the present specification, i) two of A25 to A28 are bonded to each other to form a substituted or unsubstituted C5-C10 aliphatic hydrocarbon ring, and the remaining two are hydrogen; deuterium; an unsubstituted or deuterium-substituted C1-C6 alkyl group; or an unsubstituted or deuterium-substituted C6-C20 aryl group, or ii) A25 to A28 are bonded to each other to form an unsubstituted or deuterium-substituted C6-C10 aromatic hydrocarbon ring, C1-C6 alkyl group, or a deuterium-substituted C1-C6 alkyl group.

[0447] In an exemplary embodiment of the present specification, i) two of A25 to A28 are bonded to each other to form a cyclohexane ring, and the remaining two are hydrogen; deuterium; unsubstituted or deuterium-substituted methyl; or unsubstituted or deuterium-substituted phenyl, or ii) A25 to A28 are bonded to each other to form a benzene ring that is unsubstituted or substituted with deuterium, methyl, tert-butyl, methyl substituted with deuterium, or tert-butyl substituted with deuterium; or an indene ring that is unsubstituted or substituted with methyl or tert-butyl.

[0448] In an exemplary embodiment of the present specification, i) two of A29 to A32 are bonded to each other to form a substituted or unsubstituted C5-C10 aliphatic hydrocarbon ring, and the remaining two are hydrogen; deuterium; a substituted or unsubstituted C1-C6 alkyl group; or a substituted or unsubstituted C6-C20 aryl group, or ii) A29 to A32 are bonded to each other to form a substituted or unsubstituted C6-C10 aromatic hydrocarbon ring.

[0449] In an exemplary embodiment of the present specification, i) two of A29 to A32 are bonded to each other to form a substituted or unsubstituted C5-C10 aliphatic hydrocarbon ring, and the remaining two are hydrogen; deuterium; an unsubstituted or deuterium-substituted C1-C6 alkyl group; or an unsubstituted or deuterium-substituted C6-C20 aryl group, or ii) A29 to A32 are bonded to each other to form an unsubstituted or deuterium-substituted C6-C10 aromatic hydrocarbon ring, C1-C6 alkyl group, or a deuterium-substituted C1-C6 alkyl group.

[0450] In an exemplary embodiment of the present specification, i) two of A29 to A32 are bonded to each other to form a cyclohexane ring, and the remaining two are hydrogen; deuterium; unsubstituted or deuterium-substituted methyl; or unsubstituted or deuterium-substituted phenyl, or ii) A29 to A32 are bonded to each other to form a benzene ring that is unsubstituted or substituted with deuterium, methyl, tert-butyl, methyl substituted with deuterium, or tert-butyl substituted with deuterium; or an indene ring that is unsubstituted or substituted with methyl or tert-butyl.

[0451] In an exemplary embodiment of the present specification, Formula 202 and Formula 203 Select from the following structures.

[0452]

[0453] In the structure, A33 and A34 are substituents of A21 to A32 that do not participate in ring formation, and the ring is unsubstituted or substituted with deuterium; unsubstituted or deuterium-substituted C1-C10 alkyl; or unsubstituted or deuterium-substituted C6-C20 aryl.

[0454] In an exemplary embodiment of the present specification, A21 to A24 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.

[0455] In an exemplary embodiment of the present specification, A25 to A28 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.

[0456] In an exemplary embodiment of the present specification, A29 to A32 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.

[0457] In an exemplary embodiment of the present specification, Y2 is C.

[0458] In an exemplary embodiment of the present specification, Y3 is C.

[0459] In an exemplary embodiment of the present specification, Y4 is C.

[0460] In an exemplary embodiment of the present specification, Y2 is Si.

[0461] In an exemplary embodiment of the present specification, Y3 is Si.

[0462] In an exemplary embodiment of the present specification, Y4 is Si.

[0463] In an exemplary embodiment of the present specification, Z7 and Z8 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, or bond to each other to form a substituted or unsubstituted ring.

[0464] In an exemplary embodiment of the present specification, Z7 and Z8 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted C1-C10 alkyl group; or a substituted or unsubstituted C6-C30 aryl group, or are bonded to each other to form a substituted or unsubstituted C5-C30 ring.

[0465] In an exemplary embodiment of the present specification, Z7 and Z8 are the same as or different from each other, and are each independently a substituted or unsubstituted C1-C6 alkyl group; or a substituted or unsubstituted C6-C20 aryl group, or are bonded to each other to form a substituted or unsubstituted C5-C20 ring.

[0466] In an exemplary embodiment of the present specification, Z7 and Z8 are the same as or different from each other and are each independently a methyl group; or a phenyl group which is unsubstituted or substituted with deuterium or tert-butyl, or, while being a phenyl group which is unsubstituted or substituted with deuterium or tert-butyl, are bonded to each other to form a fluorene ring which is unsubstituted or substituted with deuterium or tert-butyl; or a dibenzosilole ring which is unsubstituted or substituted with deuterium or tert-butyl.

[0467] In an exemplary embodiment of the present specification, Formula 2 contains one or more aliphatic hydrocarbon rings. Specifically, an aliphatic hydrocarbon ring may be contained in one or more of A1 to A3, or R1 to R7, R31, and A21 to A32 may be bonded with adjacent substituents to form an aliphatic hydrocarbon ring, or R4 or R5 may be an aryl group in which an aliphatic hydrocarbon ring is fused. In this case, the aliphatic hydrocarbon ring may be specifically a methyl-substituted cyclopentene ring or a methyl-substituted cyclohexene ring.

[0468] In an exemplary embodiment of the present specification, Formula 2 is asymmetric with respect to the center line. In this case, the center line is a line passing through B and the bottom benzene ring of the parent core structure. That is, in the following structure, the substituents or structures on the left and right sides are different with respect to the dotted line.

[0469]

[0470] In an exemplary embodiment of the present specification, when Formula 2 is represented by any one of Formula 204 to Formula 207, g1 of Formula 1 is 1 or more.

[0471] In an exemplary embodiment of the present specification, when Formula 2 is represented by any one of Formula 204 to Formula 207, m of Formula 1 is 1.

[0472] In an exemplary embodiment of the present specification, when Formula 2 is represented by any one of Formula 204 to Formula 207, one or more of Ar1 and Ar2 is a substituted or unsubstituted naphthyl group.

[0473] In an exemplary embodiment of the present specification, when Formula 2 is represented by Formula 201, Formula 1 includes one or more hydrogens. That is, Formula 1 is deuterated by less than 100%.

[0474] In an exemplary embodiment of the present specification, when Formula 2 is represented by Formula 201, m of Formula 1 is 1.

[0475] In an exemplary embodiment of the present specification, the compound represented by Formula 2 is any one selected from the following compounds. Specifically, the compound represented by Formula 2 is a compound represented by Formula 201.

[0476]

[0477]

[0478]

[0479]

[0480]

[0481]

[0482] In an exemplary embodiment of the present specification, the compound represented by Formula 2 is any one selected from the following compounds. Specifically, the compound represented by Formula 2 is a compound represented by Formula 202 or Formula 203.

[0483]

[0484]

[0485]

[0486]

[0487]

[0488]

[0489]

[0490]

[0491]

[0492] In an exemplary embodiment of the present specification, the compound represented by Formula 2 is any one selected from the following compounds. Specifically, the compound represented by Formula 2 is a compound represented by any one of Formulae 204 to 207.

[0493]

[0494]

[0495]

[0496]

[0497]

[0498]

[0499]

[0500]

[0501]

[0502] In an exemplary embodiment of the present specification, the compound represented by Formula 2 is any one selected from the following compounds. Specifically, the compound represented by Formula 2 is a compound represented by Formula 208.

[0503]

[0504]

[0505]

[0506]

[0507]

[0508]

[0509]

[0510]

[0511]

[0512]

[0513]

[0514]

[0515]

[0516]

[0517]

[0518]

[0519]

[0520]

[0521] According to an exemplary embodiment of the present invention, the compound of Formula 1 can be prepared as shown in the following reaction scheme 1-1 or 1-2, and the compound of Formula 2 can be prepared as shown in the following reaction scheme 2. The following reaction schemes 1-1, 1-2, and 2 describe the synthesis steps of some compounds corresponding to Formula 1 and Formula 2 of the present application, but various compounds corresponding to Formula 1 and Formula 2 of the present application can be synthesized using the synthesis steps of the following reaction schemes, the substituents can be bonded by methods known in the art, and the types and positions of the substituents and the number of the substituents can be changed according to techniques known in the art.

[0522] [Reaction Scheme 1-1]

[0523]

[0524] [Reaction Scheme 1-2]

[0525]

[0526] [Reaction Scheme 2]

[0527]

[0528] In the reaction scheme, when deuterium is introduced into a synthetic compound via a hydrogen-deuterium exchange reaction using a deuterated precursor or using a deuterated solvent in the presence of an acid catalyst or a metal catalyst, compounds of Formula 1 and Formula 2 containing deuterium may be obtained.

[0529] The organic light-emitting device of the present specification may be manufactured by a typical method and material for manufacturing an organic light-emitting device, except that the compound represented by Formula 1 and the compound represented by Formula 2 are used to form a light-emitting layer.

[0530] The light-emitting layer including the compound represented by Formula 1 and the compound represented by Formula 2 can be formed as an organic material layer not only by vacuum deposition but also by solution application. Here, the solution application method means spin coating, dip coating, inkjet printing, screen printing, spray coating, roller coating, etc., but is not limited thereto.

[0531] The organic material layer of the organic light-emitting device of the present specification may also be composed of a structure including a light-emitting layer, but may also be composed of a structure further including another organic material layer. The other organic material layer may be one or more of the following layers: a hole injection layer, a hole transport layer, a layer for simultaneously transporting and injecting holes, an electron blocking layer, a light-emitting layer, an electron transport layer, an electron injection layer, a layer for simultaneously transporting and injecting electrons, and a hole blocking layer. However, the structure of the organic light-emitting device is not limited thereto, and may include fewer or more organic material layers.

[0532] In the organic light emitting device according to an exemplary embodiment of the present specification, the light emitting layer includes the compound represented by Formula 1 as a host, and includes the compound represented by Formula 2 as a dopant.

[0533] In the organic light-emitting device according to an exemplary embodiment of the present specification, the dopant in the light-emitting layer may be included in an amount of 0.1 to 50 parts by weight, preferably 0.1 to 30 parts by weight, and more preferably 1 to 10 parts by weight, based on 100 parts by weight of the host. Within the above range, energy transfer from the host to the dopant occurs efficiently.

[0534] According to an exemplary embodiment of the present invention, the maximum emission peak of the light emitting layer including the compound represented by Formula 1 and the compound represented by Formula 2 is 400 nm to 500 nm. Specifically, the light emitting layer is a blue light emitting layer.

[0535] The structure of the organic light-emitting device of the present specification may have Figure 1 The structure shown in, but not limited to this.

[0536] Figure 1 The structure of an organic light emitting device in which a positive electrode 2 , a hole injection layer 5 , a hole transport layer 6 , a light emitting layer 3 , an electron transport layer 7 , an electron injection layer 8 and a negative electrode 4 are sequentially stacked on a substrate 1 is illustrated.

[0537] The organic light-emitting device according to the present specification can be manufactured as follows: by using a physical vapor deposition (PVD) method (e.g., sputtering or electron beam evaporation), a metal or a conductive metal oxide or an alloy thereof is deposited on a substrate to form a positive electrode, the organic material layer including the first organic material layer and the second organic material layer is formed on the positive electrode, and then a material that can be used as a negative electrode is deposited on the organic material layer. In addition to the above method, the organic electronic device can also be manufactured by sequentially depositing a negative electrode material, an organic material layer, and a positive electrode material on a substrate.

[0538] The organic material layer including the first organic material layer and the second organic material layer may also have a multilayer structure further including a hole injection layer, a hole transport layer, a layer for simultaneously injecting and transporting electrons, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, a layer for simultaneously injecting and transporting electrons, a hole blocking layer, etc. In addition, the organic material layer may be manufactured using various polymer materials by a method such as a solvent method (e.g., spin coating, dip coating, blade coating, screen printing, inkjet printing), or a thermal transfer method instead of a deposition method to include a smaller number of layers.

[0539] The positive electrode is an electrode for injecting holes, and as a positive electrode material, a material having a high work function is generally preferred to facilitate hole injection into the organic material layer. Specific examples of positive electrode materials that can be used in the present invention 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; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole and polyaniline; etc., but are not limited thereto.

[0540] The negative electrode is an electrode that injects electrons, and as a negative electrode material, a material having a low work function is generally preferred to facilitate electron injection into the organic material layer. Specific examples of negative electrode materials include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structure materials such as LiF / Al or LiO2 / Al; and the like, but are not limited thereto.

[0541] The hole injection layer is a layer for promoting the injection of holes from the positive electrode into the light-emitting layer, and the hole injection material is a material that can well receive holes from the positive electrode at a low voltage, and the highest occupied molecular orbital (HOMO) of the hole injection material is preferably a value between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrins, oligothiophenes, organic materials based on arylamines, organic materials based on hexanitrile hexaazatriphenylene, organic materials based on quinacridone, organic materials based on perylene, anthraquinone, polyaniline-based and polythiophene-based conductive polymers, etc., but are not limited thereto.

[0542] The hole transport layer can be used to promote the transport of holes. The hole transport material is suitably a material with high hole mobility that can receive holes from the positive electrode or the hole injection layer and transfer the holes to the light-emitting layer. Specific examples thereof include organic materials based on arylamine, conductive polymers, block copolymers having both conjugated and non-conjugated parts, etc., but are not limited thereto.

[0543] As the layer for simultaneously transporting and injecting holes, hole transport layer materials and / or hole injection layer materials known in the art may be used.

[0544] As the layer that simultaneously transports and injects electrons, an electron transport layer material and / or an electron injection layer material known in the art may be used.

[0545] The electron blocking layer may be disposed between the hole transport layer and the light emitting layer. For the electron blocking layer, materials known in the art may be used.

[0546] The light-emitting layer can emit red, green or blue light and can be composed of a phosphorescent material or a fluorescent material. The light-emitting material is a material that can receive holes and electrons from the hole transport layer and the electron transport layer respectively and combine the holes with the electrons to emit light in the visible light region, and is preferably a material with high quantum efficiency for fluorescence or phosphorescence. Specific examples thereof include: 8-hydroxy-quinoline aluminum complex (Alq3); carbazole-based compounds; diphenylethylene compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo-based azoles, benzothiazole-based and benzimidazole-based compounds; poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorenes; rubrene; and the like, but are not limited thereto.

[0547] Examples of host materials for the light-emitting layer include fused aromatic ring derivatives or heterocyclic compounds, etc. Specifically, examples of fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and examples of heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but examples thereof are not limited thereto.

[0548] When the light-emitting layer emits red light, a phosphorescent material such as bis(1-phenylisoquinoline) iridium acetylacetonate (PIQIr(acac)), bis(1-phenylquinoline) iridium acetylacetonate (PQIr(acac)), tris(1-phenylquinoline) iridium (PQIr), or platinum octaethylporphyrin (PtOEP), or a fluorescent material such as tris(8-hydroxyquinoline) aluminum (Alq3) can be used as a light-emitting dopant, but the light-emitting dopant is not limited thereto. When the light-emitting layer emits green light, a phosphorescent material such as fac tris(2-phenylpyridine) iridium (Ir(ppy)3) or a fluorescent material such as tris(8-hydroxyquinoline) aluminum (Alq3) can be used as a light-emitting dopant, but the light-emitting dopant is not limited thereto. When the light-emitting layer emits blue light, a phosphorescent material such as (4,6-F2ppy)2Irpic, or a fluorescent material such as spiro-DPVBi, spiro-6P, distyrylbenzene (DSB), distyrylarylene (DSA), a PFO-based polymer or a PPV-based polymer can be used as a light-emitting dopant, but the light-emitting dopant is not limited thereto.

[0549] A hole blocking layer may be provided between the electron transport layer and the light emitting layer, and a material known in the art may be used.

[0550] The electron transport layer is used to promote the transport of electrons. The electron transport material is suitably a material with high electron mobility, which can well receive electrons from the negative electrode and transfer the electrons to the light-emitting layer. Specific examples thereof include: Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic free radical compounds; hydroxyflavone-metal complexes; and the like, but are not limited thereto.

[0551] The electron injection layer is used to promote the injection of electrons. The electron injection material is preferably a compound that has the ability to transport electrons, the effect of injecting electrons from the negative electrode, and the excellent effect of injecting electrons into the light-emitting layer or the light-emitting material, and the ability to form a thin film is also excellent. Specific examples thereof include fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenyl methane, anthrone and the like and their derivatives, metal complex compounds, nitrogen-containing 5-membered ring derivatives and the like, but not limited thereto.

[0552] Examples of metal complex compounds include 8-hydroxyquinoline lithium, bis(8-hydroxyquinoline) zinc, bis(8-hydroxyquinoline) copper, bis(8-hydroxyquinoline) manganese, tris(8-hydroxyquinoline) aluminum, tris(2-methyl-8-hydroxyquinoline) aluminum, tris(8-hydroxyquinoline) gallium, bis(10-hydroxybenzo[h]quinoline) beryllium, bis(10-hydroxybenzo[h]quinoline) zinc, bis(2-methyl-8-quinoline) gallium chloride, bis(2-methyl-8-quinoline)(o-cresol) gallium, bis(2-methyl-8-quinoline)(1-naphthol) aluminum, bis(2-methyl-8-quinoline)(2-naphthol) gallium, and the like, but are not limited thereto.

[0553] The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a dual emission type according to the materials used.

[0554] Embodiments of the invention

[0555] Hereinafter, the present specification will be described in detail with reference to the embodiments for specifically describing the present specification. However, the embodiments according to the present specification can be modified in various forms, and should not be interpreted as limiting the scope of the present specification to the embodiments described in detail below. The embodiments of the present specification are provided to explain the present specification more completely to those of ordinary skill in the art.

[0556] Synthesis Example 1. Synthesis of BH-1

[0557]

[0558] <1-a> Synthesis of Compound BH-1-a

[0559] 9-phenylanthracene (45g) and AlCl (9g) are put into C D (900ml), and the resulting solution is stirred for 2 hours. After the reaction is completed, D O (60ml) is added thereto, and the resulting solution is stirred for 30 minutes, and then trimethylamine (6ml) is added thereto dropwise. The reaction solution is transferred to a separating funnel, and extracted with water and toluene. With the extract MgSO Drying, the residue is then recrystallized with ethyl acetate to obtain BH-1-a with a productive rate of 67%.

[0560] <1-b> Synthesis of Compound BH-1-b

[0561] After compound BH-1-a (30 g, 111 mmol) was dispersed in 500 ml dimethylformamide, a solution of N-bromosuccinimide (19.9 g, 111 mmol) dissolved in 50 ml dimethylformamide was slowly added dropwise thereto. After reacting at room temperature for 2 hours, 1 L of water was added dropwise thereto. When a solid was produced, the solid was filtered and then dissolved in ethyl acetate, and the resulting solution was placed in a separatory funnel and then washed several times with distilled water. The resulting product was recrystallized in EA to obtain compound BH-1-b (32 g, yield: 83%).

[0562] <1-c> Synthesis of Compound BH-1

[0563] After compound BH-1-b (32 g, 92 mmol) and dibenzo [b, d] furan-2-yl boronic acid (19.6 g, 92 mmol) were dissolved in THF (450 ml), Pd (PPh 3 ) 4 (5.3 g, 4.6 mmol) and 100 ml of 2M K 2 CO 3 aqueous solution were added thereto, and the resulting solution was refluxed for 24 hours. The reaction solution was cooled, and the organic layer was extracted with ethyl acetate and then dried over anhydrous magnesium sulfate. The organic solvent was removed under reduced pressure, and the residue was recrystallized with EA to obtain compound BH-1 (25 g, yield 62%).

[0564] Synthesis Example 2. Synthesis of BH-2

[0565]

[0566] <2-a> Synthesis of Compound BH-2-a

[0567] 9-Bromoanthracene (50 g, 194 mmol) and dibenzo[b,d]furan-1-ylboronic acid (41.2 g, 194 mmol) were dissolved in 1,4-dibromoanthracene. After 2 hours, add Pd (PPh 3) 4 (11.23g, 9.7mmol) and 200ml 2M K 2 CO 3 aqueous solution, and reflux the resulting solution for 24 hours. Allow the reaction solution to cool, and extract the organic layer with ethyl acetate, then dry over anhydrous magnesium sulfate. Remove the organic solvent under reduced pressure, and use column chromatography to purify the residue to obtain compound BH-2-a (54g, yield 81%).

[0568] <2-b> Synthesis of Compound BH-2-b

[0569] The synthesized compound BH-2-a (54g), AlCl (10.8g) were put into C6D6 (1080ml), and the resulting solution was stirred for 2 hours. After the reaction was completed, D2O (80ml) was added thereto, and the resulting solution was stirred for 30 minutes, and then trimethylamine (8ml) was added dropwise thereto. The reaction solution was transferred to a separating funnel, and extracted with water and toluene. The extract was dried with MgSO4, and then the residue was recrystallized with ethyl acetate to obtain BH-2-b (43g, yield 76%).

[0570] <2-c> Synthesis of compound BH-2-c

[0571] After compound BH-2-b (43g, 119mmol) was dispersed in 500ml dimethylformamide, a solution of N-bromosuccinimide (21.2g, 119mmol) dissolved in 100ml dimethylformamide was slowly added dropwise thereto. After reacting at room temperature for 2 hours, 1L of water was added dropwise thereto. When a solid was produced, the solid was filtered and then dissolved in ethyl acetate, and the resulting solution was placed in a separatory funnel and then washed several times with distilled water. The resulting product was recrystallized in EA to obtain compound BH-2-c (37g, yield: 83%).

[0572] <2-d> Synthesis of Compound BH-2

[0573] Compound BH-2-c (37 g, 84 mmol) and naphthalene-2-ylboronic acid (14.5 g, 84 mmol) were dissolved in 1,4-dihydro- After 100ml of KCO3 solution and 100ml of ethanol (500ml), Pd(PPh3)4 (4.9g, 4.2mmol) and 100ml of K2CO3 aqueous solution were added thereto, and the resulting solution was refluxed for 24 hours. The reaction solution was cooled, and the organic layer was extracted with ethyl acetate and then dried over anhydrous magnesium sulfate. The organic solvent was removed under reduced pressure, and the residue was recrystallized in EA to obtain compound BH-2 (16g, yield 55%). [M+H + ]=486.3

[0574] Synthesis Example 3. Synthesis of BH-3

[0575]

[0576] <3-a> Synthesis of Compound BH-3-a

[0577] Compound BH-3-a was obtained by synthesis and purification in the same manner as in Synthesis Example 2-a, except that dibenzo[b,d]furan-1-ylboronic acid was changed to (3-(naphthalen-1-yl)phenyl)boronic acid.

[0578] <3-b> Synthesis of Compound BH-3-b

[0579] Compound BH-3-b was obtained by performing synthesis and purification in the same manner as in Synthesis Example 2-b, except that Compound BH-2-a was changed to Compound BH-3-a.

[0580] <3-c> Synthesis of compound BH-3-c

[0581] Compound BH-3-c was obtained by performing synthesis and purification in the same manner as in Synthesis Example 2-c, except that Compound BH-2-b was changed to Compound BH-3-b.

[0582] <3-d> Synthesis of Compound BH-3

[0583] Compound BH-3 was obtained by synthesis and purification in the same manner as in Synthesis Example 2-d, except that Compound BH-2-c was changed to Compound BH-3-c, and naphthane-2-ylboronic acid was changed to dibenzo[b,d]furan-1-ylboronic acid. [M+H + ]=566.3

[0584] Synthesis Example 4. Synthesis of BH-4

[0585]

[0586] <4-a> Synthesis of Compound BH-4-a

[0587] Compound BH-4-a was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-a, except that 9-phenylanthracene was changed to 9-(naphthalene-1-yl)anthracene.

[0588] <4-b> Synthesis of Compound BH-4-b

[0589] Compound BH-4-b was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-b, except that Compound BH-1-a was changed to Compound BH-4-a.

[0590] <4-c> Synthesis of Compound BH-4

[0591] Compound BH-4 was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-c, except that Compound BH-1-b was changed to Compound BH-4-b.

[0592] Synthesis Example 5. Synthesis of BH-5

[0593]

[0594] <5-a> Synthesis of Compound BH-5-a

[0595] Compound BH-5-a was obtained by synthesis and purification in the same manner as in Synthesis Example 2-a, except that dibenzo[b,d]furan-1-ylboronic acid was changed to dibenzo[b,d]furan-4-ylboronic acid.

[0596] <5-b> Synthesis of Compound BH-5-b

[0597] Compound BH-5-b was obtained by performing synthesis and purification in the same manner as in Synthesis Example 2-b, except that Compound BH-2-a was changed to Compound BH-5-a.

[0598] <5-c> Synthesis of compound BH-5-c

[0599] Compound BH-5-c was obtained by performing synthesis and purification in the same manner as in Synthesis Example 2-c, except that Compound BH-2-b was changed to Compound BH-5-b.

[0600] <5-d> Synthesis of Compound BH-5

[0601] Compound BH-5 was obtained by synthesis and purification in the same manner as in Synthesis Example 2-d, except that Compound BH-2-c was changed to Compound BH-5-c. [M+H + ]=486.3

[0602] Synthesis Example 6. Synthesis of BH-6

[0603]

[0604] <6-a> Synthesis of Compound BH-6-a

[0605] Compound BH-6-a was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-a, except that 9-phenylanthracene was changed to 9-(naphthalene-2-yl)anthracene.

[0606] <6-b> Synthesis of Compound BH-6-b

[0607] Compound BH-6-b was obtained by performing synthesis and purification in the same manner as in Synthesis Example 1-b, except that Compound BH-1-a was changed to Compound BH-6-a.

[0608] <6-c> Synthesis of Compound BH-6

[0609] Compound BH-6 was obtained by synthesis and purification in the same manner as in Synthesis Example 1-c, except that Compound BH-1-b was changed to Compound BH-6-b, and dibenzo[b,d]furan-2-ylboronic acid was changed to dibenzo[b,d]furan-3-ylboronic acid. [M+H + ]=486.3

[0610] Synthesis Example 7. Synthesis of BH-7

[0611]

[0612] <7-c> Synthesis of Compound BH-7

[0613] Compound BH-7 was obtained by synthesis and purification in the same manner as in Synthesis Example 1-c, except that Compound BH-1-b was changed to Compound BH-4-b, and dibenzo[b,d]furan-2-ylboronic acid was changed to (4-(dibenzo[b,d]furan-2-yl)phenyl)boronic acid. [M+H + ]=562.3

[0614] Synthesis Example 8. Synthesis of BH-8

[0615]

[0616] <8-a> Synthesis of Compound BH-8

[0617] Compound BH-8 was obtained by synthesis and purification in the same manner as in Synthesis Example 1-c, except that dibenzo[b,d]furan-2-ylboronic acid was changed to (8-phenyldibenzo[b,d]furan-2-yl)boronic acid. [M+H + ]=509.3

[0618] Synthesis Example 9. Synthesis of BH-9

[0619]

[0620] <9-a> Synthesis of Compound BH-9-a

[0621] 9-Bromo-10-(naphthalen-1-yl)anthracene (30 g, 78 mmol) and (4-(naphthalen-2-yl)phenyl)boronic acid (19.4 g, 78 mmol) were dissolved in 1,4-dihydro-1,4-diol. After 2 hours, add Pd (PPh 3) 4 (4.5g, 3.9mmol) and 100ml 2M K 2 CO 3 aqueous solution, and reflux the resulting solution for 24 hours. Allow the reaction solution to cool, and extract the organic layer with ethyl acetate, and then dry with anhydrous magnesium sulfate. The solution is recrystallized in EA to obtain compound BH-9-a (25g, yield 63%).

[0622] <9-b> Synthesis of Compound BH-9

[0623] The synthesized compound BH-9-a (25 g) and AlCl3 (5 g) were placed in C6D6 (500 ml), and the resulting solution was stirred for 2 hours. After the reaction was completed, D2O (40 ml) was added thereto, the resulting solution was stirred for 30 minutes, and then trimethylamine (4 ml) was added dropwise thereto. The reaction solution was transferred to a separatory funnel and extracted with water and toluene. The extract was dried with MgSO4, and then the residue was recrystallized with ethyl acetate to obtain BH-9 (18 g, 68%). [M+H + ]=533.4

[0624] Synthesis Example 10. Synthesis of BH-10

[0625]

[0626] <10-a> Synthesis of Compound BH-10

[0627] Compound BH-10 was obtained by synthesis and purification in the same manner as in Synthesis Example 1-c, except that Compound BH-1-b was changed to Compound BH-4-b, and dibenzo[b,d]furan-2-ylboronic acid was changed to (3-(naphthalen-2-yl)phenyl)boronic acid. [M+H + ]=522.3

[0628] Synthesis Example 11. Synthesis of BH-11

[0629]

[0630] <11-a> Synthesis of Compound BH-11

[0631] Compound BH-11 was obtained by synthesis and purification in the same manner as in Synthesis Example 1-c, except that Compound BH-1-b was changed to Compound BH-4-b, and dibenzo[b,d]furan-2-ylboronic acid was changed to naphthalene-2-ylboronic acid. [M+H + ]=446.3

[0632] Synthesis Example 12. Synthesis of BH-12

[0633]

[0634] <12-a> Synthesis of Compound BH-12-a

[0635] 2-bromo-9,10-diphenylanthracene (30 g) and AlCl3 (6 g) were placed in C6D6 (600 ml), and the resulting solution was stirred for 2 hours. After the reaction was completed, D2O (45 ml) was added thereto, the resulting solution was stirred for 30 minutes, and then trimethylamine (4.5 ml) was added dropwise thereto. The reaction solution was transferred to a separatory funnel and extracted with water and toluene. The extract was dried with MgSO4, and then the residue was purified by column chromatography to obtain BH-12-a (19 g, 61%).

[0636] <12-b> Synthesis of Compound BH-12

[0637] BH-12-a (19 g, 45 mmol) and naphthalene-1-ylboronic acid (7.7 g, 45 mmol) were dissolved in 1,4-dihydro- After being added to alkane (200ml), Pd(PPh3)4 (2.6g, 2.2mmol) and 500ml 2M K2CO3 aqueous solution were added thereto, and the resulting solution was refluxed for 24 hours. The reaction solution was cooled, and the organic layer was extracted with ethyl acetate and then dried over anhydrous magnesium sulfate. The resulting product was recrystallized in EA to obtain compound BH-12 (13g, yield 61%). [M+H + ]=474.3

[0638] Synthesis Example 13. Synthesis of BH-13

[0639]

[0640] <13-a> Preparation of Compound BH-13-a

[0641] After 2-phenylanthracene (50g, 197mmol) was dispersed in 500ml dimethylformamide, a solution of N-bromosuccinimide (35g, 197mmol) dissolved in 50ml dimethylformamide was slowly added dropwise thereto. After reacting at room temperature for 2 hours, 1L water was added dropwise thereto. When a solid was produced, the solid was filtered and then dissolved in ethyl acetate, and the resulting solution was placed in a separating funnel and then washed several times with distilled water. The solution was recrystallized in EA to obtain compound BH-13-a (56g, yield 85%).

[0642] <13-b> Synthesis of Compound BH-13-b

[0643] Compound BH-13-a (56 g, 168 mmol) and phenylboronic acid (20.5 g, 168 mmol) were dissolved in 1,4-dihydro- After 2 hours, add 1% 2-nitropropene (5% pyrrolidone) (5% pyrrolidone) (6% pyrrolidone) (7% pyrrolidone) (8% pyrrolidone) (1% pyrrolidone) (2% pyrrolidone) (1% pyrrolidone) (2% pyrrolidone) (8% pyrrolidone) (1% pyrrolidone) (2% pyrrolidone) (8% pyrrolidone) (1% pyrrolidone) (2% pyrrolidone) (8% pyrrolidone) (1% pyrrolidone) (8 ...8% pyrrolidone) (8% pyrrolidone

[0644] <13-c> Synthesis of Compound BH-13-c

[0645] The synthesized compound BH-13-b (45g) and AlCl (9g) are put into C6D6 (900ml), and the resulting solution is stirred for 2 hours. After the reaction is completed, D2O (70ml) is added thereto, and the resulting solution is stirred for 30 minutes, and then trimethylamine (6ml) is added dropwise thereto. The reaction solution is transferred to a separating funnel, and extracted with water and toluene. The extract is dried with MgSO4, and then the residue is recrystallized with ethyl acetate to obtain BH-13-c (34g, yield 71%).

[0646] <13-d> Synthesis of compound BH-13-d

[0647] After compound BH-13-c (34 g, 98 mmol) was dispersed in 450 ml dimethylformamide, a solution of N-bromosuccinimide (17.4 g, 98 mmol) dissolved in 50 ml dimethylformamide was slowly added dropwise thereto. After reacting at room temperature for 2 hours, 1 L of water was added dropwise thereto. When a solid was produced, the solid was filtered and then dissolved in ethyl acetate, and the resulting solution was placed in a separatory funnel and then washed several times with distilled water. The resulting product was recrystallized in EA to obtain compound BH-13-d (33 g, yield: 79%).

[0648] <13-e> Synthesis of Compound BH-13

[0649] Compound BH-13-d (33 g, 77 mmol) and naphthalene-1-ylboronic acid (13.3 g, 77 mmol) were dissolved in 1,4-dihydro- After being added to alkane (350ml), Pd(PPh3)4 (4.5g, 3.9mmol) and 70ml 2M K2CO3 aqueous solution were added thereto, and the resulting solution was refluxed for 24 hours. The reaction solution was cooled, and the organic layer was extracted with ethyl acetate and then dried over anhydrous magnesium sulfate. The resulting product was recrystallized in EA to obtain compound BH-13 (21g, yield 57%). [M+H + ]=474.3

[0650] Synthesis Example 14. Synthesis of Compound BH-14

[0651]

[0652] <14-a> Synthesis of Compound BH-14-a

[0653] 2-Chloroanthracene (80g) and AlCl (16g) are put into C D (1600ml), and the resulting solution is stirred for 2 hours. After the reaction is completed, D O (120ml) is added thereto, and the resulting solution is stirred for 30 minutes, and then trimethylamine (12ml) is added dropwise thereto. The reaction solution is transferred to a separating funnel, and extracted with water and toluene. By MgSO for the extract Drying, then the residue is recrystallized with ethyl acetate to obtain BH-14-a (65g, 78% yield).

[0654] <14-b> Synthesis of Compound BH-14-b

[0655] BH-14-a (65 g, 293 mmol) and phenylboronic acid (35.7 g, 293 mmol) were dissolved in 1,4-dihydro- After 2 hours, 2-(tri-tert-butylphosphine) palladium (0) (0.75g, 1.5mmol) and 300ml 2M KCO aqueous solution were added thereto, and the resulting solution was refluxed for 24 hours. The reaction solution was cooled, and the organic layer was extracted with ethyl acetate, then dried over anhydrous magnesium sulfate. The organic solvent was removed under reduced pressure, and column chromatography was used to purify the residue to obtain compound BH-14-b (56g, yield 73%).

[0656] <14-c> Synthesis of compound BH-14-c

[0657] After BH-14-b (56g, 213mmol) was dispersed in 800ml dimethylformamide, a solution of N-bromosuccinimide (37.8g, 213mmol) dissolved in 200ml dimethylformamide was slowly added dropwise thereto. After reacting at room temperature for 2 hours, 2.5L water was added dropwise thereto. When a solid was produced, the solid was filtered and then dissolved in ethyl acetate, and the resulting solution was placed in a separatory funnel and then washed several times with distilled water. The resulting product was recrystallized in EA to obtain compound BH-14-c (51g, yield: 70%).

[0658] <14-d> Synthesis of compound BH-14-d

[0659] BH-14-c (51 g, 149 mmol) and dibenzo[b,d]furan-2-ylboronic acid (31.7 g, 149 mmol) were dissolved in 1,4-dihydrofuran-2-ylboronic acid. After 2 hours, add 1% 2-nitropropane (700ml), add Pd (PPh3) 4 (8.6g, 7.5mmol) and 180ml 2M K2CO3 aqueous solution, and reflux the resulting solution for 24 hours. Allow the reaction solution to cool, and extract the organic layer with ethyl acetate, and then dry with anhydrous magnesium sulfate. The resulting product is recrystallized in EA to obtain compound BH-14-d (47g, yield: 73%).

[0660] <14-e> Synthesis of compound BH-14-e

[0661] After BH-14-d (47g, 110mmol) was dispersed in 450ml dimethylformamide, a solution of N-bromosuccinimide (19.5g, 110mmol) dissolved in 100ml dimethylformamide was slowly added dropwise thereto. After reacting at room temperature for 2 hours, 1.5L water was added dropwise thereto. When a solid was produced, the solid was filtered and then dissolved in ethyl acetate, and the resulting solution was placed in a separatory funnel and then washed several times with distilled water. The resulting product was recrystallized in EA to obtain compound BH-14-e (39g, yield: 70%).

[0662] <14-f> Synthesis of Compound BH-14

[0663] BH-14-e (39 g, 77 mmol) and naphthalene-1-ylboronic acid (13.2 g, 77 mmol) were dissolved in 1,4-dibromopropane. After 2 hours of ... + ]=554.2

[0664] Synthesis Example 15. Synthesis of Compound BH-15

[0665]

[0666] <15-a> Synthesis of Compound BH-15-a

[0667] Compound BH-15-a was obtained by synthesis and purification in the same manner as in Synthesis Example 14-d, except that dibenzo[b,d]furan-2-ylboronic acid was changed to (phenyl-d5)boronic acid.

[0668] <15-b> Synthesis of Compound 15-b

[0669] Compound BH-15-b was obtained by synthesis and purification in the same manner as in Synthesis Example 14-e, except that BH-14-d was changed to BH-15-a.

[0670] <15-c> Synthesis of Compound BH-15

[0671] Compound BH-15 was obtained by synthesis and purification in the same manner as in Synthesis Example 14-f, except that BH-14-e was changed to BH-15-b, and naphthylboronic acid was changed to dibenzo[b,d]furan-2-ylboronic acid. [M+H + ]=509.3

[0672] Synthesis Example 16. Synthesis of Compound BH-16

[0673]

[0674] <16-a> Synthesis of Compound BH-16

[0675] Compound BH-16 was obtained by synthesis and purification in the same manner as in Synthesis Example 14-f, except that BH-14-e was changed to BH-15-b, and naphthylboronic acid was changed to dibenzo[b,d]furan-1-ylboronic acid. [M+H + ]=509.3

[0676] Synthesis Example 17. Synthesis of Compound BH-17

[0677]

[0678] <17-a> Synthesis of Compound BH-17-a

[0679] Compound BH-17-a was obtained by synthesis and purification in the same manner as in Synthesis Example 14-d, except that dibenzo[b,d]furan-2-ylboronic acid was changed to (naphthalen-1-yl-d7)boronic acid.

[0680] <17-b> Synthesis of Compound BH-17-b

[0681] Compound BH-17-b was obtained by synthesis and purification in the same manner as in Synthesis Example 14-e, except that BH-14-d was changed to BH-17-a.

[0682] <17-c> Synthesis of Compound 17

[0683] Compound BH-17 was obtained by synthesis and purification in the same manner as in Synthesis Example 14-f, except that BH-14-e was changed to BH-17-b, and naphthylboronic acid was changed to dibenzo[b,d]furan-2-ylboronic acid. [M+H + ]=561.3

[0684] Synthesis Example 18. Synthesis of Compound BH-18

[0685]

[0686] <18-a> Synthesis of Compound BH-18-a

[0687] Compound BH-18-a was synthesized by performing synthesis in the same manner as in Synthesis Example 13-a, except that 2-phenylanthracene was changed to 2-(naphthalene-1-yl)anthracene.

[0688] <18-b> Synthesis of Compound BH-18-b

[0689] Compound BH-18-b was synthesized by performing synthesis in the same manner as in Synthesis Example 13-b, except that Compound BH-13-a was changed to BH-18-a, and phenylboronic acid was changed to [1,1′-biphenyl]-3-ylboronic acid.

[0690] <18-c> Synthesis of compound BH-18-c

[0691] Compound BH-18-c was synthesized by performing synthesis in the same manner as in Synthesis Example 13-c, except that Compound BH-13-b was changed to BH-18-b.

[0692] <18-d> Synthesis of compound BH-18-d

[0693] Compound BH-18-d was synthesized by performing synthesis in the same manner as in Synthesis Example 13-d, except that Compound BH-13-c was changed to BH-18-c.

[0694] <18-e> Synthesis of Compound BH-18

[0695] Compound BH-18 was synthesized by performing synthesis in the same manner as in Synthesis Example 13-e, except that Compound BH-13-d was changed to Compound BH-18-d, and naphthane-1-ylboronic acid was changed to dibenzo[b,d]furan-2-ylboronic acid. [M+H + ]=646.4

[0696] Synthesis Example 19. Synthesis of Compound BH-19

[0697]

[0698] <19-a> Synthesis of Compound BH-19

[0699] Compound BH-19 was obtained by synthesis and purification in the same manner as in Synthesis Example 1-c, except that BH-1-b was changed to 2-(10-bromoanthracene-9-yl)dibenzo[b,d]furan, and dibenzo[b,d]furan-2-ylboronic acid was changed to (phenyl-d5)boronic acid. [M+H + ]=426.2

[0700] Synthesis Example 20. Synthesis of Compound BH-20

[0701]

[0702] <20-a> Synthesis of Compound BH-20

[0703] Compound BH-20 was obtained by synthesis and purification in the same manner as in Synthesis Example 1-c, except that BH-1-b was changed to 9-bromo-10-(naphthalene-2-yl)anthracene, and dibenzo[b,d]furan-2-ylboronic acid was changed to (naphthalene-1-yl-d7)boronic acid. [M+H + ]=438.2

[0704] Synthesis Example 21. Synthesis of Compound BH-21

[0705]

[0706] <21-a> Synthesis of Compound BH-21

[0707] Compound BH-21 was obtained by synthesis and purification in the same manner as in Synthesis Example 12-b, except that BH-12-a was changed to 2-bromo-9,10-diphenylanthracene, and naphthane-1-ylboronic acid was changed to (naphthane-1-yl-d7)boronic acid. [M+H + ]=464.2

[0708] Synthesis Example 22. Synthesis of Compound BH-22

[0709]

[0710] <22-a> Synthesis of Compound BH-22-a

[0711] Compound BH-13-a (50 g, 150 mmol) and (phenyl-d5) boronic acid (19.0 g, 150 mmol) were dissolved in 1,4-dihydro- After 2 hours, add 1% 2-nitropropene (750ml), add Pd (PPh 3) 4 (8.7g, 7.5mmol) and 150ml 2M K 2 CO 3 aqueous solution, and reflux the resulting solution for 24 hours. Allow the reaction solution to cool, and extract the organic layer with ethyl acetate, then dry over anhydrous magnesium sulfate. Remove the organic solvent under reduced pressure, and use column chromatography to purify the residue to obtain compound BH-22-a (36g, yield 71%).

[0712] <22-b> Preparation of compound BH-22-b

[0713] After BH-22-a (36 g, 107 mmol) was dispersed in 500 ml dimethylformamide, a solution of N-bromosuccinimide (19.1 g, 107 mmol) dissolved in 50 ml dimethylformamide was slowly added dropwise thereto. After reacting at room temperature for 2 hours, 1 L of water was added dropwise thereto. When a solid was produced, the solid was filtered and then dissolved in ethyl acetate, and the resulting solution was placed in a separatory funnel and then washed several times with distilled water. The resulting product was recrystallized in EA to obtain compound BH-22-b (34 g, yield: 76%).

[0714] <22-c> Synthesis of Compound BH-22

[0715] Compound BH-22-b (34 g, 102 mmol) and dibenzo[b,d]furan-1-ylboronic acid (21.6 g, 102 mmol) were dissolved in 1,4-dihydrofuran-1-ylboronic acid. After 2 hours of 2 hours of heating, the mixture was stirred for 2 hours. After ... + ]=502.2

[0716] Synthesis Example 23. Synthesis of Compound BH-23

[0717]

[0718] <23-a> Synthesis of Compound BH-23

[0719] Compound BH-23 was obtained by performing synthesis in the same manner as in Synthesis Example 22-c, except that dibenzo[b,d]furan-1-ylboronic acid was changed to dibenzo[b,d]furan-2-ylboronic acid. [M+H + ]=502.2

[0720] Synthesis Example 24. Synthesis of BD-1

[0721]

[0722] <24-a> Synthesis of BD-1-a

[0723] Under a nitrogen atmosphere, 50 g of 4-(tert-butyl)-N-(4-(tert-butyl)-phenyl)-2-methylaniline, 35.1 g of 3-bromo-5-chlorophenol, 32.5 g of sodium tert-butoxide, and 1.73 g of bis(tri-tert-butylphosphine)palladium(0) were put into 500 ml of toluene, and the resulting mixture was stirred under reflux for 6 hours. After the reaction was completed, the resulting product was extracted and then purified with an ethyl acetate:hexane column, and then recrystallized to obtain 42.0 g of BD-1-a (yield 58%).

[0724] <24-b> Synthesis of BD-1-b

[0725] Under a nitrogen atmosphere, 42 g of BD-1-a, 35.6 g of 5-(tert-butyl)-N-(4-(tert-butyl)phenyl)-[1,1'-biphenyl]-2-amine, 19.1 g of sodium tert-butoxide, and 1.02 g of bis(tri-tert-butylphosphine)palladium(0) were put into 300 ml of toluene, and the resulting mixture was stirred under reflux for 6 hours. After the reaction was completed, the resulting product was extracted, and then purified with an ethyl acetate:hexane column, and then recrystallized to obtain 51.0 g of BD-1-b (yield 69%).

[0726] <24-c> Synthesis of BD-1-c

[0727] After 51g BD-1-b, 10.2g 5% Pt / C, 300ml toluene, and 700ml D2O were placed in a high pressure reactor, the reactor was filled with hydrogen. After the reactor was heated to 180°C, the reaction was carried out for 24 hours. After the reaction was completed, the catalyst was filtered through a tetracalcium aluminate pad and then extracted. The resulting product was purified with an ethyl acetate: hexane column and then recrystallized to obtain 32.0g BD-1-c. (yield 61%).

[0728] <24-d> Synthesis of BD-1-d

[0729] Under a nitrogen atmosphere, 32 g of BD-1-c, 19.1 g of 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride, and 17.5 g of potassium carbonate were placed in 400 ml of chloromethane, and the resulting mixture was stirred at room temperature for 3 hours. After the reaction was completed, the resulting product was extracted and then purified with an ethyl acetate: hexane column to obtain 38 g of BD-1-d (yield 86%).

[0730] <24-e> Synthesis of BD-1-e

[0731] Under a nitrogen atmosphere, 38 g of BD-1-d, 7.5 g of 4a,9a-dimethyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole-5,6,7,8-d4, 7.02 g of sodium tert-butoxide and 0.37 g of bis(tri-tert-butylphosphine)palladium(0) were put into 150 ml of toluene, and the resulting mixture was stirred under reflux for 6 hours. After the reaction was completed, the resulting product was extracted and then purified with an ethyl acetate:hexane column and then recrystallized to obtain 25.0 g of BD-1-e (yield 72%).

[0732] <24-f> Synthesis of BD-1

[0733] Under a nitrogen atmosphere, after dissolving 25 g of BD-1-e in 200 ml of dichlorobenzene, 6.3 ml of boron triiodide was introduced therein. The resulting mixture was heated to 160° C. and then stirred for 6 hours. After the reaction was completed, dichlorobenzene was distilled off under reduced pressure, and the residue was then extracted with ethyl acetate / water. The extract was purified with an ethyl acetate: hexane column and then recrystallized to obtain 6.2 g of BD-1 (yield 25%). MS [M+H] + = 952.73

[0734] Synthesis Example 25. Synthesis of BD-2

[0735]

[0736] <25-a> Synthesis of BD-2-a

[0737] After 50 g of N-(4-(tert-butyl)-2-(methyl-d3)phenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-amine, 10 g of 5% Pt / C, 300 ml of toluene, and 700 ml of D2O were placed in a high pressure reactor, the reactor was filled with hydrogen. After the reactor was heated to 180°C, the reaction was carried out for 24 hours. After the reaction was completed, the catalyst was filtered through a tetracalcium aluminate pad and then extracted. The extract was purified with an ethyl acetate: hexane column and then recrystallized to obtain 43.0 g of BD-2-a. (yield 84%).

[0738] <25-b> Synthesis of BD-2-b

[0739] After 43 g of BD-2-a, 27.1 g of 1-bromo-3,5-dichlorobenzene, 23.0 g of sodium tert-butoxide, and 1.23 g of bis(tri-tert-butylphosphine)palladium(0) were put into 400 ml of toluene under a nitrogen atmosphere, the resulting mixture was stirred under reflux for 6 hours. After the reaction was completed, the resulting product was extracted and then purified with an ethyl acetate:hexane column and then recrystallized to obtain 41 g of BD-2-b (yield 68%).

[0740] <25-c> Synthesis of BD-2-c

[0741] After 41 g of BD-2-b, 24.7 g of bis(4-tert-butyl)phenyl-2,3,5,6-d4)amine, 16.4 g of sodium tert-butoxide, and 0.87 g of bis(tri-tert-butylphosphine)palladium(0) were put into 300 ml of toluene under a nitrogen atmosphere, the resulting mixture was stirred under reflux for 6 hours. After the reaction was completed, the resulting product was extracted and then purified with an ethyl acetate:hexane column and then recrystallized to obtain 45 g of BD-2-c (yield 70%).

[0742] <25-d> Synthesis of BD-2-d

[0743] After 45 g of BD-2-c, 10.7 g of bis(phenyl-d5)amine, 11.4 g of sodium tert-butoxide, and 0.61 g of bis(tri-tert-butylphosphine)palladium(0) were placed in 200 ml of toluene under a nitrogen atmosphere, the resulting mixture was stirred under reflux for 6 hours. After the reaction was completed, the resulting product was extracted and then purified with an ethyl acetate:hexane column and then recrystallized to obtain 37 g of BD-2-d (yield 69%).

[0744] <25-e> Synthesis of BD-2

[0745] After 37 g of BD-2-d was dissolved in 300 ml of dichlorobenzene under a nitrogen atmosphere, 9.8 ml of boron triiodide was introduced therein. The resulting mixture was heated to 160° C. and then stirred for 6 hours. After the reaction was completed, dichlorobenzene was distilled off under reduced pressure, and the residue was extracted with ethyl acetate / water. The extract was purified with an ethyl acetate: hexane column and then recrystallized to obtain 8.7 g of BD-2 (yield 23%). MS [M+H] + = 905.7

[0746] Synthesis Example 26. Synthesis of BD-3

[0747]

[0748] <26-a> Synthesis of BD-3-a

[0749] Compound BD-3-a was obtained by synthesis and purification in the same manner as in Synthesis Example 25-a, except that N-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-2,2-dimethyl-2,3-dihydro-1H-indene-5-amine was used instead of N-(4-(tert-butyl)-2-(methyl-d3)phenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-amine.

[0750] <26-b> Synthesis of BD-3-b

[0751] Compound BD-3-b was obtained by synthesis and purification in the same manner as in Synthesis Example 25-b, except that BD-3-a and 1-bromo-2,3-dichloro-5-(methyl-d3)benzene were used instead of BD-2-a and 1-bromo-3,5-dichlorobenzene, respectively.

[0752] <26-c> Synthesis of BD-3-c

[0753] Compound BD-3-c was obtained by synthesis and purification in the same manner as in Synthesis Example 25-c, except that BD-3-b was used instead of BD-2-b.

[0754] <26-d> Synthesis of BD-3

[0755] After 12 g of BD-3-c was put into 120 ml of toluene under a nitrogen atmosphere, the temperature was lowered to 0° C., and then 17.7 ml of tert-butyl lithium (1.7 M) was slowly added dropwise thereto. After 1 hour, 2.86 ml of boron tribromide was added dropwise thereto, and then the temperature was increased to 60° C., and then the resulting mixture was stirred for 12 hours. After the reaction was completed, the resulting product was extracted, and then purified with an ethyl acetate: hexane column, and then recrystallized to obtain 2.2 g of BD-3 (yield 19%). MS [M+H] + = 767.6

[0756] Synthesis Example 27. Synthesis of BD-4

[0757]

[0758] <27-a> Synthesis of BD-4-a

[0759] After 50 g of 5-(tert-butyl)-[1,1'-biphenyl]-2-amine, 48.22 g of 1-bromo-3-(tert-butyl)benzene-2,4,5,6-d4, 42.7 g of sodium tert-butoxide, and 2.27 g of bis(tri-tert-butylphosphine)palladium(0) were put into 700 mL of toluene under a nitrogen atmosphere, the resulting mixture was stirred under reflux for 6 hours. After the reaction was completed, the resulting product was extracted and then purified with an ethyl acetate:hexane column and then recrystallized to obtain 54 g of BD-4-a (yield 68%).

[0760] <27-b> Synthesis of BD-4-b

[0761] After 54 g of BD-4-a, 36.1 g of 1-bromo-2,3-dichloro-5-methylbenzene-4,6-d2, 28.7 g of sodium tert-butoxide, and 1.52 g of bis(tri-tert-butylphosphine)palladium(0) were put into 500 ml of toluene under a nitrogen atmosphere, the resulting mixture was stirred under reflux for 6 hours. After the reaction was completed, the resulting product was extracted and then purified with an ethyl acetate:hexane column and then recrystallized to obtain 59 g of BD-4-b (yield 76%).

[0762] <27-c> Synthesis of BD-4-c

[0763] After 59 g of BD-4-b, 29.1 g of 6-(tert-butyl)-4a,9a-dimethyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole, 21.7 g of sodium tert-butoxide, and 1.15 g of bis(tri-tert-butylphosphine)palladium(0) were put into 400 ml of toluene under a nitrogen atmosphere, the resulting mixture was stirred under reflux for 6 hours. After the reaction was completed, the resulting product was extracted and then purified with an ethyl acetate:hexane column and then recrystallized to obtain 51 g of BD-4-c (yield 61%).

[0764] <27-d> Synthesis of BD-4

[0765] After 10 g of BD-4-c was placed in 100 ml of toluene under a nitrogen atmosphere, the temperature was lowered to 0° C., and then 24.9 ml of tert-butyl lithium (1.7 M) was slowly added dropwise thereto. After 1 hour, 4.01 ml of boron tribromide was added dropwise thereto, and then the temperature was increased to 60° C., and then the resulting mixture was stirred for 12 hours. After the reaction was completed, the resulting product was extracted, and then purified with an ethyl acetate: hexane column, and then recrystallized to obtain 3.5 g of BD-4 (yield 23%). MS [M+H] + = 716.5

[0766] Synthesis Example 37. Synthesis of BD-5

[0767]

[0768] <37-a> Synthesis of BD-5-a

[0769] After 50 g of 6-bromo-4a,9a-dimethyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole and 22.7 g of (phenyl-d5) boronic acid were dissolved in 600 ml of THF, 1.83 g of bis(tri-tert-butylphosphine)palladium(0) and 150 ml of 2M K2CO3 aqueous solution were added thereto, and the resulting mixture was stirred under reflux for 24 hours. After the reaction was completed, the resulting product was extracted, then purified with an ethyl acetate: hexane column, and then recrystallized to obtain 42 g of BD-5-a (yield 83%).

[0770] <37-b> Synthesis of BD-5-b

[0771] After 42 g of BD-5-a, 33.7 g of 1-bromo-3,5-dichlorobenzene-2,4,6-d3, 28.6 g of sodium tert-butoxide, and 1.51 g of bis(tri-tert-butylphosphine)palladium(0) were put into 500 ml of toluene under a nitrogen atmosphere, the resulting mixture was stirred under reflux for 6 hours. After the reaction was completed, the resulting product was extracted and then purified with an ethyl acetate:hexane column and then recrystallized to obtain 36 g of BD-5-b (yield 56%).

[0772] <37-c> Synthesis of BD-5-c

[0773] After 36 g of BD-5-b, 20 g of N-(4-(tert-butyl)phenyl)-3-methylaniline, 16.1 g of sodium tert-butoxide, and 0.85 g of bis(tri-tert-butylphosphine)palladium(0) were placed in 300 ml of toluene under a nitrogen atmosphere, the resulting mixture was stirred under reflux for 6 hours. After the reaction was completed, the resulting product was extracted and then purified with an ethyl acetate:hexane column, and then recrystallized to obtain 32 g of BD-5-c (yield 60%).

[0774] <37-d> Synthesis of BD-5-d

[0775] After 32 g of BD-5-c, 16.4 g of bis(4-tert-butyl)phenyl-2,3,5,6-d4)amine, 10.9 g of sodium tert-butoxide, and 0.58 g of bis(tri-tert-butylphosphine)palladium(0) were put into 200 ml of toluene under a nitrogen atmosphere, the resulting mixture was stirred under reflux for 6 hours. After the reaction was completed, the resulting product was extracted and then purified with an ethyl acetate:hexane column and then recrystallized to obtain 34 g of BD-5-d (yield 67%).

[0776] <37-e> Synthesis of BD-5

[0777] Under a nitrogen atmosphere, after 34 g of BD-5-d was dissolved in 300 ml of dichlorobenzene, 9.2 ml of boron triiodide was introduced therein. The resulting mixture was heated to 160° C. and then stirred for 6 hours. After the reaction was completed, dichlorobenzene was distilled off under reduced pressure, and the residue was extracted with ethyl acetate / water. The extract was purified with an ethyl acetate: hexane column and then recrystallized to obtain 9.3 g of BD-5 (yield 27%). MS [M+H] + = 893.6

[0778] Synthesis Example 28. Synthesis of BD-6

[0779]

[0780] <28-a> Synthesis of BD-6-a

[0781] After 50 g of 5-(tert-butyl)-N-(4-(tert-butyl)phenyl)benzo[b]thiophene-3-amine, 10 g of 5% Pt / C, 300 ml of toluene, and 700 ml of D2O were placed in a high pressure reactor, the reactor was filled with hydrogen. After the reactor was heated to 180°C, the reaction was carried out for 24 hours. After the reaction was completed, the catalyst was filtered through a tetracalcium aluminate pad and then extracted. The resulting product was purified with an ethyl acetate: hexane column and then recrystallized to obtain 43.0 g of BD-6-a. (yield 84%).

[0782] <28-b> Synthesis of BD-6-b

[0783] After 43 g of BD-6-a, 30.1 g of 1-bromo-2,3-dichloro-5-(methyl-d3)benzene, 24 g of sodium tert-butoxide, and 1.27 g of bis(tri-tert-butylphosphine)palladium(0) were placed in 400 ml of toluene under a nitrogen atmosphere, the resulting mixture was stirred under reflux for 6 hours. After the reaction was completed, the resulting product was extracted and then purified with an ethyl acetate:hexane column and then recrystallized to obtain 39 g of BD-6-b (yield 62%).

[0784] <28-c> Synthesis of BD-6-c

[0785] After 39 g of BD-6-b, 22.3 g of 3-(tert-butyl)-N-(4-(tert-butyl)phenyl-2,3,5,6-d4)benzene-2,4,5,6-d4-amine, 14.8 g of sodium tert-butoxide, and 0.78 g of bis(tri-tert-butylphosphine)palladium(0) were put into 300 ml of toluene under a nitrogen atmosphere, the resulting mixture was stirred under reflux for 6 hours. After the reaction was completed, the resulting product was extracted and then purified with an ethyl acetate:hexane column and then recrystallized to obtain 42 g of BD-6-c (yield 72%).

[0786] <28-d> Synthesis of BD-6

[0787] After 10 g of BD-6-c was placed in 100 ml of toluene under a nitrogen atmosphere, the temperature was lowered to 0° C., and then 15.5 ml of tert-butyl lithium (1.7 M) was slowly added dropwise thereto. After 1 hour, 2.49 ml of boron tribromide was added dropwise thereto, and then the temperature was increased to 60° C., and then the resulting mixture was stirred for 12 hours. After the reaction was completed, the resulting product was extracted, and then purified with an ethyl acetate: hexane column, and then recrystallized to obtain 2.4 g of BD-6 (yield 25%). MS [M+H] + = 732.5

[0788] Synthesis Example 29. Synthesis of BD-7

[0789]

[0790] <29-a> Synthesis of BD-7-a

[0791] After 50 g of 5-(tert-butyl)-N-(4-(2-phenylpropan-2-yl)phenyl)benzo[b]thiophene-3-amine, 10 g of 5% Pt / C, 300 ml of toluene, and 700 ml of D2O were placed in a high pressure reactor, the reactor was filled with hydrogen. After the reactor was heated to 180°C, the reaction was carried out for 24 hours. After the reaction was completed, the catalyst was filtered through a tetracalcium aluminate pad and then extracted. The resulting product was purified with an ethyl acetate: hexane column and then recrystallized to obtain 38.0 g of BD-7-a. (yield 74%).

[0792] <29-b> Synthesis of BD-7-b

[0793] After 38 g of BD-7-a, 22.3 g of 1-bromo-2,3-dichloro-5-methylbenzene-4,6-d2, 17.7 g of sodium tert-butoxide, and 0.94 g of bis(tri-tert-butylphosphine)palladium(0) were put into 300 ml of toluene under a nitrogen atmosphere, the resulting mixture was stirred under reflux for 6 hours. After the reaction was completed, the resulting product was extracted and then purified with an ethyl acetate:hexane column and then recrystallized to obtain 35 g of BD-7-b (yield 66%).

[0794] <29-c> Synthesis of BD-7-c

[0795] Under a nitrogen atmosphere, 39 g of BD-7-b, 20.1 g of 5-(tert-butyl)-N-(4-(tert-butyl)phenyl-2,3,5,6-d4)benzofuran-2,4,6,7-d4-3-amine, 11.7 g of sodium tert-butoxide, and 0.62 g of bis(tri-tert-butylphosphine)palladium(0) were placed in 200 ml of toluene, and the resulting mixture was stirred under reflux for 6 hours. After the reaction was completed, the resulting product was extracted and then purified with an ethyl acetate:hexane column, and then recrystallized to obtain 31 g of BD-7-c (yield 58%).

[0796] <29-d> Synthesis of BD-7

[0797] After 31 g of BD-7-c was put into 120 ml of toluene under a nitrogen atmosphere, the temperature was lowered to 0° C., and then 42.2 ml of tert-butyl lithium (1.7 M) was slowly added dropwise thereto. After 1 hour, 6.80 ml of boron tribromide was added dropwise thereto, and then the temperature was increased to 60° C., and then the resulting mixture was stirred for 12 hours. After the reaction was completed, the resulting product was extracted, and then purified with an ethyl acetate: hexane column, and then recrystallized to obtain 4.5 g of BD-7 (yield 15%). MS [M+H] + = 838.6

[0798] Synthesis Example 30. Synthesis of BD-8

[0799]

[0800] <30-a> Synthesis of BD-8-a

[0801] Under nitrogen conditions, 50g of 1,3-dibromo-5-(methyl-d3)benzene was dissolved in 500mL of diethyl ether, and the resulting solution was cooled to -78°C. Then, 124mL of 1.6M n-BuLi hexane solution was slowly added dropwise thereto, and the resulting solution was stirred at -78°C for 2 hours. 100.1g of dichlorodiphenylsilane was placed therein, and the resulting solution was stirred for 10 hours while slowly heating it to room temperature. The reaction was terminated by placing distilled water therein, 100mL of diethyl ether was further placed therein for extraction, and the extract was then dried over anhydrous sodium sulfate. The resulting product was purified by column chromatography (eluent: hexane / ethyl acetate = 50% / 50% (volume ratio)) to obtain 67g of BD-8-a.

[0802] <30-b> Synthesis of BD-8-b

[0803] After 67 g of BD-8-a, 37.8 g of 4-(tert-butyl)aniline, 24.4 g of sodium tert-butoxide, and 1.3 g of bis(tri-tert-butylphosphine)palladium(0) were put into 600 ml of toluene under a nitrogen atmosphere, the resulting mixture was stirred under reflux for 6 hours. After the reaction was completed, the resulting product was extracted and then purified with an ethyl acetate:hexane column and then recrystallized to obtain 65 g of BD-8-b (yield 77%).

[0804] <30-c> Synthesis of BD-8-c

[0805] After 65g BD-8-b, 13g 5% Pt / C, 500ml toluene, and 1200ml D2O were placed in a high pressure reactor, the reactor was filled with hydrogen. After the reactor was heated to 180°C, the reaction was carried out for 24 hours. After the reaction was completed, the catalyst was filtered through a tetracalcium aluminate pad and then extracted. The resulting product was purified with an ethyl acetate: hexane column and then recrystallized to obtain 51.0g BD-8-c. (yield 77%).

[0806] Synthesis of <30-d>BD-8-d

[0807] After 51 g of BD-8-c, 24.5 g of 1,3-dibromo-5-(tert-butyl)-2-chlorobenzene, 36.1 g of sodium tert-butoxide, and 1.92 g of bis(tri-tert-butylphosphine)palladium(0) were put into 250 ml of toluene under a nitrogen atmosphere, the resulting mixture was stirred under reflux for 6 hours. After the reaction was completed, the resulting product was extracted and then purified with an ethyl acetate:hexane column and then recrystallized to obtain 46 g of BD-8-d (yield 73%).

[0808] <30-e> Synthesis of BD-8

[0809] After 31 g of BD-8-d was put into 180 ml of toluene under a nitrogen atmosphere, the temperature was lowered to 0° C., and then 64.1 ml of tert-butyl lithium (1.7 M) was slowly added dropwise thereto. After 1 hour, 10.3 ml of boron tribromide was added dropwise thereto, and then the temperature was increased to 60° C., and then the resulting mixture was stirred for 12 hours. After the reaction was completed, the resulting product was extracted, and then purified with an ethyl acetate: hexane column, and then recrystallized to obtain 11 g of BD-8 (yield 25%). MS [M+H] + = 816.6

[0810] Synthesis Example 31. Synthesis of BD-9

[0811]

[0812] <31-a> Synthesis of BD-9-a

[0813] Under nitrogen conditions, 50g of 1,3-dibromo-5-(tert-butyl)benzene was dissolved in 500mL of diethyl ether, and the resulting solution was cooled to -78°C. Then, 107mL of 1.6Mn-BuLi hexane solution was slowly added dropwise thereto, and the resulting solution was stirred at -78°C for 2 hours. 100.1g of 5,5-dichloro-5H-dibenzo[b,d]silole was placed therein, and the resulting solution was stirred for 10 hours while slowly heating to room temperature. The reaction was terminated by placing distilled water therein, 100mL of diethyl ether was further placed therein for extraction, and the extract was then dried over anhydrous sodium sulfate. The extract was purified by silica gel column chromatography (eluent: hexane / ethyl acetate = 50% / 50% (volume ratio)) to obtain 66g of BD-9-a.

[0814] <31-b> Synthesis of BD-9-b

[0815] After 66 g of BD-9-a, 32.6 g of 4-(tert-butyl)aniline, 21.0 g of sodium tert-butoxide, and 1.1 g of bis(tri-tert-butylphosphine)palladium(0) were placed in 500 ml of toluene under a nitrogen atmosphere, the resulting mixture was stirred under reflux for 6 hours. After the reaction was completed, the resulting product was extracted and then purified with an ethyl acetate:hexane column and then recrystallized to obtain 53 g of BD-9-b (yield 66%).

[0816] <31-c> Synthesis of BD-9-c

[0817] After 53g BD-9-b, 10g 5% Pt / C, 500ml toluene, and 1200ml D2O were placed in a high pressure reactor, the reactor was filled with hydrogen. After the reactor was heated to 180°C, the reaction was carried out for 24 hours. After the reaction was completed, the catalyst was filtered through a tetracalcium aluminate pad and then extracted. The resulting product was purified with an ethyl acetate: hexane column and then recrystallized to obtain 45.0g BD-9-c. (yield 83%).

[0818] <31-d> Synthesis of BD-9-d

[0819] After 45 g of BD-9-c, 13.4 g of 1-bromo-3,5-dichlorobenzene, 28.6 g of sodium tert-butoxide, and 1.52 g of bis(tri-tert-butylphosphine)palladium(0) were placed in 200 ml of toluene under a nitrogen atmosphere, the resulting mixture was stirred under reflux for 6 hours. After the reaction was completed, the resulting product was extracted and then purified with an ethyl acetate:hexane column and then recrystallized to obtain 31 g of BD-9-d (yield 60%).

[0820] <31-e> Synthesis of BD-9-e

[0821] Under a nitrogen atmosphere, after 31 g of BD-9-d was dissolved in 300 ml of dichlorobenzene, 8.5 ml of boron triiodide was introduced therein. The resulting mixture was heated to 160° C. and then stirred for 6 hours. After the reaction was completed, dichlorobenzene was distilled off under reduced pressure, and the residue was extracted with ethyl acetate / water. The extract was purified with an ethyl acetate: hexane column and then recrystallized to obtain 7.3 g of BD-9-e (yield 23%).

[0822] <31-f> Synthesis of BD-9

[0823] Under nitrogen atmosphere, after 7.3 g of BD-9-e, 1.7 g of 4a,9a-dimethyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole-5,6,7,8-d4, 1.6 g of sodium tert-butoxide, and 0.1 g of bis(tri-tert-butylphosphine)palladium(0) were put into 50 ml of toluene, the resulting mixture was stirred under reflux for 6 hours. After the reaction was completed, the resulting product was extracted and then purified with an ethyl acetate:hexane column and then recrystallized to obtain 4.3 g of BD-9 (yield 49%). MS [M+H] + = 1044.7

[0824] Synthesis Example 32. Synthesis of BD-10

[0825]

[0826] <32-a> Synthesis of BD-10-a

[0827] BD-10-a was obtained by synthesizing in the same manner as in Synthesis Example 24-e, except that 4a,9a-dimethyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole-5,6,7,8,-d4 was changed to 4a,9a-dimethyl-2,3,4,4a,9,9a-hexahydro-1H-carbazole.

[0828] <32-b> Synthesis of BD-10

[0829] BD-10 was obtained by synthesizing in the same manner as in Synthesis Example 24-f, except that compound BD-1-e was changed to compound BD-10-a. MS [M+H] + = 949.71

[0830] Synthesis Example 33. Synthesis of BD-11

[0831]

[0832] <33-a> Synthesis of BD-11-a

[0833] Compound BD-11-a was obtained by performing synthesis in the same manner as in Synthesis Example 25-d, except that bis(phenyl-d5)amine was changed to diphenylamine.

[0834] <33-b> Synthesis of BD-11

[0835] BD-11 was obtained by synthesizing in the same manner as in Synthesis Example 25-e, except that compound BD-2-d was changed to compound BD-11-a. MS [M+H] + = 895.7

[0836] Synthesis Example 34. Synthesis of BD-12

[0837]

[0838] <34-a> Synthesis of BD-12-a

[0839] Compound BD-12-a was obtained by synthesizing in the same manner as in Synthesis Example 25-b, except that BD-2-a and 1-bromo-3,5-dichlorobenzene were changed to BD-3-a and 1-bromo-2,3-dichloro-5-methylbenzene, respectively.

[0840] <34-b> Synthesis of BD-12-b

[0841] Compound BD-12-b was obtained by performing synthesis in the same manner as in Synthesis Example 25-c, except that BD-2-b was changed to BD-12-a.

[0842] <34-c> Synthesis of BD-12

[0843] Compound BD-12 was obtained by synthesizing in the same manner as in Synthesis Example 26-d, except that BD-3-c was changed to BD-12-b. MS [M+H] + = 764.6

[0844] Synthesis Example 35. Synthesis of BD-13

[0845]

[0846] <35-a> Synthesis of BD-13-a

[0847] Compound BD-13-a is obtained by synthesizing in the same manner as in Synthesis Example 27-a, except that 5-(tert-butyl)-[1,1'-biphenyl]-2-amine and 1-bromo-3-(tert-butyl)benzene-2,4,5,6-d4 are changed to 5-(tert-butyl)-[1,1'-biphenyl]-3,4,6-d3-2-amine and 1-bromo-3-(tert-butyl)benzene, respectively.

[0848] <35-b> Synthesis of BD-13-b

[0849] Compound BD-13-b was obtained by performing synthesis in the same manner as in Synthesis Example 27-b, except that BD-4-a was changed to BD-13-a.

[0850] <35-c> Synthesis of BD-13-c

[0851] Compound BD-13-c was obtained by performing synthesis in the same manner as in Synthesis Example 27-c, except that BD-4-b was changed to BD-13-b.

[0852] <35-d> Synthesis of BD-13

[0853] Compound BD-13 was obtained by synthesizing in the same manner as in Synthesis Example 27-d, except that BD-4-c was changed to BD-13-c. MS [M+H] + = 716.5

[0854] Synthesis Example 36. Synthesis of BD-14

[0855]

[0856] <36-a> Synthesis of BD-14-a

[0857] Compound BD-14-a was obtained by synthesizing in the same manner as in Synthesis Example 28-b, except that 1-bromo-2,3-dichloro-5-(methyl-d3)benzene was changed to 1-bromo-2,3-dichloro-5-methylbenzene.

[0858] <36-b> Synthesis of BD-14-b

[0859] Compound BD-14-b was obtained by performing synthesis in the same manner as in Synthesis Example 28-c, except that BD-6-b was changed to BD-14-a.

[0860] <36-c> Synthesis of BD-14

[0861] Compound BD-14 was obtained by synthesizing in the same manner as in Synthesis Example 28-d, except that BD-6-c was changed to BD-14-b. MS [M+H] + = 729.5

[0862] Example 1

[0863] A thin coating having a thickness of The glass substrate of indium tin oxide (ITO) is put into the distilled water dissolved with cleaning agent and carries out ultrasonic cleaning.In this case, the product manufactured by Fischer Co. is used as cleaning agent, and the distilled water filtered twice by the filter manufactured by Millipore Co. is used as distilled water.After ITO is washed for 30 minutes, ultrasonic cleaning is repeated twice by using distilled water for 10 minutes.After using distilled water washing to complete, ultrasonic cleaning is carried out by using isopropyl alcohol, acetone and methanol solvent, and the products therefrom is dried and then transported to plasma washing machine.In addition, nitrogen plasma is used to wash substrate for 5 minutes, and then transported to vacuum deposition device.

[0864] The following HTL1 compound was thermally vacuum deposited on the thus prepared ITO transparent electrode to have The following HAT compound and the following compound HTL2 are sequentially vacuum deposited on the hole injection layer to have a thickness of and A thickness of , thereby forming a first hole transport layer and a second hole transport layer.

[0865] Subsequently, BH-1 as a host and BD-1 as a dopant (weight ratio 95:5) were simultaneously vacuum deposited on the second hole transport layer to form a layer with a thickness of of the luminous layer.

[0866] Subsequently, the ETL is vacuum deposited to have Subsequently, LiF is vacuum deposited to have a thickness of Aluminum is then deposited to have a thickness of to form a negative electrode, thereby manufacturing an organic light-emitting device.

[0867] The structures of the compounds used in the examples are as follows.

[0868]

[0869] Examples 2 to 59

[0870] An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compounds described in the following Tables 1 to 6 were each used instead of BH-1 and BD-1 as a host and a dopant of the light-emitting layer, respectively.

[0871]

[0872]

[0873]

[0874]

[0875] Comparative Examples 1 to 29

[0876] An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compounds described in the following Tables 1 to 6 were each used instead of BH-1 and BD-1 as a host and a dopant of the light-emitting layer, respectively.

[0877]

[0878]

[0879] In the organic light-emitting devices of the examples and comparative examples, at 10 mA / cm 2 The driving voltage and luminous efficiency were measured at a current density of 20 mA / cm 2 The time (LT) to reach 95% compared to the initial luminance was measured at a current density of 1.5 Å, and the results are shown in the following Tables 1 to 6. In the following Tables 1 to 6, D substitution rate means deuterium substitution rate.

[0880] [Table 1]

[0881]

[0882] The lifespans of the devices made of BH-1 in which anthracene is substituted with deuterium, and BD-1, BD-4, or BD-6 in which deuterium is substituted, are shown to be the longest in Examples 1 to 3. Although Examples 4 and 5 also have longer lifespans than Comparative Examples 1 to 3, since anthracene of the host is not substituted with deuterium, the lifespans are not long compared to the substitution rate.

[0883] [Table 2]

[0884]

[0885] All of Examples 6 to 16 showed excellent device performance and long service life. Although Example 16 also had a long service life, because the anthracene portion of BH-11 was not substituted with deuterium, the service life relative to the substitution rate was not good compared to the service life of Example 6. However, Examples 6 to 16 showed better performance than Comparative Examples 4 to 9.

[0886] [Table 3]

[0887]

[0888] All of Examples 16-1 to 21 showed long service life characteristics. In the case of Example 21, because the anthracene of the host was not substituted with deuterium, the service life was slightly shorter than the substitution rate. However, all of Examples 16-1 to 21 showed better performance than Comparative Examples 10 to 13.

[0889] [Table 4]

[0890]

[0891] All of Examples 22 to 28 exhibited longer service life characteristics than Comparative Examples 14 to 17, among which Example 28 had a reduced service life increase rate compared to the substitution rate because anthracene was not substituted with deuterium.

[0892] [Table 5]

[0893]

[0894] All of Examples 29 to 43 exhibited longer service life characteristics than Comparative Examples 18 to 23, among which Examples 40 to 43 had a reduced service life increase rate compared to the substitution rate because anthracene was not substituted with deuterium.

[0895] [Table 6]

[0896]

[0897] Examples 44 and 45 have a longer service life than that of Comparative Example 24. However, the service life increase rate in Example 44 is greater than the deuterium substitution rate. This is because when the N-para position of dimethylhydrocarbazole is substituted with deuterium, there is an effect of extending the service life longer. In the same case, when the N-para position of diphenylamine is not substituted with deuterium, Examples 46 and 47 also show a longer service life.

[0898] In the case of Examples 48 to 51, when the deuterium-substituted methyl group was substituted, the rate of increase in the service life relative to the deuterium substitution rate was greater than when the methyl group was substituted at the para position of boron.

[0899] Examples 52 to 55 also have longer service lives than Comparative Examples 26 and 27, and when the para-position of N is deuterium, the increase rate is higher than when the para-position of N is hydrogen.

[0900] Examples 56 to 59 also have longer lifetimes than Comparative Examples 28 and 29, but the rate of increase varies depending on the deuterium substitution position of the dopant.

[0901] As in the case of Examples 48 to 51, when the para position of boron is -CD3, the service life is longer than when the para position of boron is -CH3.

[0902] Although the preferred exemplary embodiments of the present specification have been described above, the present invention is not limited thereto, and various modifications may be made and performed within the scope of the claims and detailed description of the present invention, and these modifications also fall within the scope of the present invention.

Claims

1. An organic light-emitting device, comprising: Positive electrode; Negative electrode; and An organic material layer including a light-emitting layer is disposed between the positive electrode and the negative electrode, The light-emitting layer comprises a compound represented by the following formula 1 and a compound represented by the following formula 201, 202-1, 204, 206 or 208: In formula 1, L1 to L3 are the same as or different from each other and are each independently a direct bond; or a deuterium-substituted or unsubstituted phenylene group, Ar1 to Ar3 are the same as or different from each other and are each independently a deuterium-substituted or unsubstituted phenyl group; a deuterium-substituted or unsubstituted biphenyl group; a deuterium-substituted or unsubstituted naphthyl group; or a dibenzofuranyl group which is substituted or unsubstituted with one or two or more substituents selected from deuterium and phenyl, m is 0 or 1, When m is 0, deuterium is substituted at the position of -L3-Ar3. g1 is 7, [Formula 201] [Formula 202-1] [Formula 204] [Formula 206] [Formula 208] In equations 201, 202-1, 204, 206 and 208, R1 and R2 are the same as or different from each other and are each independently hydrogen; deuterium; methyl substituted or unsubstituted by deuterium; tert-butyl substituted or unsubstituted by deuterium; phenyl substituted or unsubstituted by deuterium, or bonded to an adjacent substituent to form a cyclohexane ring or cyclopentane ring substituted or unsubstituted by one or two or more substituents selected from deuterium and methyl, R3 is hydrogen; deuterium; methyl group substituted or unsubstituted by deuterium; tert-butyl group substituted or unsubstituted by deuterium; diphenylamino group substituted or unsubstituted by one or two or more substituents selected from deuterium and tert-butyl; or a group represented by formula 2-A-2, [Formula 2-A-2] T11 to T14 are the same as or different from each other and are each independently hydrogen or deuterium, Y1 is C, p1 is 0 or 1, T15 and T16 are the same as or different from each other and are each independently hydrogen; deuterium; or methyl, Cy5 is a cyclohexane ring, T24 and T25 are the same as or different from each other and are each independently hydrogen; deuterium; or methyl substituted or unsubstituted with deuterium, T29 is hydrogen or deuterium, t29 is an integer from 0 to 4, and when t29 is 2 or more, the substituents in the brackets are the same as or different from each other, R4 and R5 are the same as or different from each other, and are each independently a group represented by Chemical Formula 3-A, [Formula 3-A] R31 is hydrogen; deuterium; tert-butyl substituted or unsubstituted by deuterium; isopropyl substituted or unsubstituted by a substituent selected from one or two or more substituents selected from deuterium and phenyl or two or more substituents of the above substituents connected to each other, r31 is an integer from 0 to 5, and when r31 is 2 or more, the substituents in the brackets are the same as or different from each other, R6 and R7 are the same as or different from each other and are each independently hydrogen; deuterium; deuterium-substituted or unsubstituted methyl; deuterium-substituted or unsubstituted tert-butyl; or deuterium-substituted or unsubstituted phenyl, A21 to A24 are the same as or different from each other and are each independently hydrogen; deuterium; a methyl group which may be substituted or unsubstituted with deuterium, or bond with an adjacent substituent to form a cyclohexane ring which may be substituted or unsubstituted with one or two or more substituents selected from deuterium and a methyl group, X1 and X2 are the same or different from each other and are each independently O or S, Y5 is Si, Z7 and Z8 are the same as or different from each other and are each independently hydrogen; deuterium; methyl substituted or unsubstituted by deuterium; tert-butyl substituted or unsubstituted by deuterium; phenyl substituted or unsubstituted by deuterium, or bonded to an adjacent substituent to form a dibenzosilole ring substituted or unsubstituted by deuterium or tert-butyl, r1 is an integer from 0 to 4, r2 is an integer from 0 to 4, r3 is an integer from 0 to 3, r1' is an integer from 0 to 3, r2' is an integer from 0 to 3, r6 is an integer from 0 to 5, and r7 is an integer from 0 to 5, and when r1 to r3, r1', r2', r6 and r7 are each 2 or more, the substituents in brackets are the same as or different from each other, Formula 1 contains at least one deuterium, and Formulas 201, 202-1, 204, 206, and 208 contain at least one deuterium. 2 . The organic light emitting device according to claim 1 , wherein Formula 1 is deuterated by 40% or more. 3 . The organic light emitting device according to claim 1 , wherein Formulas 201, 202-1, 204, 206 and 208 are deuterated by 40% or more. The organic light emitting device according to claim 1 , wherein -L1-Ar1 and -L2-Ar2 are different from each other. The organic light emitting device according to claim 1 , wherein m is 1. 6 . The organic light-emitting device according to claim 1 , wherein at least one of Ar1 and Ar2 is a dibenzofuranyl group which is unsubstituted or substituted with a phenyl group. The organic light emitting device according to claim 1 , wherein at least one of Ar1 and Ar2 is a naphthyl group.

8. The organic light-emitting device according to claim 1, wherein the compound represented by Formula 1 is any one selected from the following compounds:

9. The organic light-emitting device according to claim 1, wherein the compound represented by Formula 1 is any one selected from the following compounds:

10. The organic light-emitting device according to claim 1, wherein the compound represented by Formula 201 is any one selected from the following compounds:

11. The organic light-emitting device according to claim 1, wherein the compound represented by Formula 202-1 is any one selected from the following compounds:

12. The organic light-emitting device according to claim 1, wherein the compound represented by Formula 204 or Formula 206 is any one selected from the following compounds:

13. The organic light-emitting device according to claim 1, wherein the compound represented by Formula 208 is any one selected from the following compounds:

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