Heterocyclic compounds and organic light emitting elements comprising the same

Abstract

The present specification relates to a heterocyclic compound of Chemical Formula 1 and an organic light emitting element including the same.

Description

[0001] Cross-reference of related applications

[0002] This application claims priority and benefits over Korean Patent Application No. 10-2021-0066212, filed with the Korean Intellectual Property Office on May 24, 2021, the entire contents of which are incorporated herein by reference. Technical Field

[0003] This specification relates to a heterocyclic compound and an organic light-emitting element comprising said heterocyclic compound. Background Technology

[0004] Electroluminescent (EL) elements are self-emissive display elements that have the advantages of wide viewing angle, high response speed, and excellent contrast.

[0005] Organic light-emitting elements (OLEDs) have a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to an OLED with this structure, electrons and holes injected from the two electrodes combine and pair in the organic thin film, emitting light as they annihilate. The organic thin film can be formed as a single layer or multiple layers as needed.

[0006] Organic thin film materials can possess light-emitting properties as needed. For example, as materials for organic thin films, compounds capable of forming a light-emitting layer independently can be used, or compounds capable of functioning as the host or dopant in a host-dopant-based light-emitting layer can be used. In addition, compounds capable of performing hole injection, hole transfer, electron blocking, electron transfer, electron injection, and similar functions can also be used as materials for organic thin films.

[0007] To enhance the performance, lifespan, or efficiency of organic light-emitting elements, there is a continuous need to develop organic thin film materials. Summary of the Invention

[0008] Technical issues

[0009] This specification aims to provide a heterocyclic compound and an organic light-emitting element comprising said heterocyclic compound.

[0010] Technical solutions

[0011] One embodiment of this specification provides a heterocyclic compound of the following chemical formula 1.

[0012] [Chemical Formula 1]

[0013]

[0014] In chemical formula 1,

[0015] R1 to R10 may be the same as or different from each other, and each is independently hydrogen; deuterium; halogen group; cyano group; -Si(R11)(R12)(R13); -N(R14)(R15); substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl.

[0016] R11 through R15 are each independently hydrogen; deuterium; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl.

[0017] At least one of R1 to R10 is -(L)lN(R24)(R25),

[0018] At least one of the remaining parts of R1 to R10 is a substituted or unsubstituted C6 to C60 aryl group.

[0019] L is a direct bond; a substituted or unsubstituted C6 to C60 arylene; or a substituted or unsubstituted C2 to C60 heteroarylene.

[0020] l is an integer from 1 to 3, and when l is 2 or greater than 2, L are either the same or different from each other.

[0021] R24 and R25 may be the same as or different from each other, and each is independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0022] Another embodiment of this specification provides an organic light-emitting element, the organic light-emitting element comprising: a first electrode; a second electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the plurality of organic material layers comprises the heterocyclic compound of formula 1.

[0023] Beneficial effects

[0024] The heterocyclic compounds described in this specification can be used as materials for the organic material layer of organic light-emitting elements (OLEDs). These heterocyclic compounds can function as hole injection materials, hole transfer materials, light-emitting materials, electron transfer materials, electron injection materials, hole blocking materials, electron blocking materials, charge-generating materials, or the like in OLEDs. Specifically, these compounds can be used as hole transfer materials or electron blocking materials in OLEDs.

[0025] When the heterocyclic compound of Formula 1 is included and used in the hole transfer layer or electron blocking layer of an organic light-emitting element, an organic light-emitting element with excellent driving voltage and lifetime can be provided.

[0026] Specifically, in the heterocyclic compound of Formula 1, benzo[kl]xanthones are substituted with amino and aryl groups, which delocalizes the highest occupied molecular orbital (HOMO) energy level, thereby increasing hole transfer capability and stabilizing HOMO energy.

[0027] Therefore, when a heterocyclic compound of Formula 1 is used as a material for the hole transfer layer or electron blocking layer in an organic light-emitting element, an appropriate energy level and band gap will be formed, thereby increasing the excitons in the light-emitting region, and the effects of reducing the driving voltage of the element, enhancing the light efficiency, and increasing the lifetime of the element through the thermal stability of the compound will be achieved. Attached Figure Description

[0028] Figures 1 to 4 Each of the above diagrams illustrates a stacked structure of an organic light-emitting element according to one embodiment of this specification.

[0029] [Symbol Explanation]

[0030] 100:Substrate;

[0031] 200: Anode;

[0032] 300: Organic material layer;

[0033] 301: Hole injection layer;

[0034] 302: Hole transfer layer;

[0035] 303: Electron blocking layer;

[0036] 304: Emissive layer;

[0037] 305: Hole-blocking layer;

[0038] 306: Electron transfer layer;

[0039] 307: Electron injection layer;

[0040] 400: Cathode. Detailed Implementation

[0041] This instruction manual will be described in more detail below.

[0042] In this specification, the description that a particular part "includes" a particular component means that it may further include other components, and unless otherwise stated to the contrary, other components are not excluded.

[0043] The term "substitution" means that the hydrogen atom bonded to the carbon atom of a compound is replaced by another substituent, and the position of substitution is not limited, as long as it is the position where the hydrogen atom is substituted (i.e., the position where the substituent can be substituted). When two or more substituents are substituted, the two or more substituents may be the same as or different from each other.

[0044] In this specification, "substituted or unsubstituted" means substituted or unsubstituted by one or more substituents selected from the group consisting of deuterium; halogen group; cyano group; C1 to C60 alkyl group; C2 to C60 alkenyl group; C2 to C60 alkynyl group; C3 to C60 cycloalkyl group; C2 to C60 heterocycloalkyl group; C6 to C60 aryl group; C2 to C60 heteroaryl group; silyl group; phosphine oxide group; and amine group, or unsubstituted or substituted by substituents linked to two or more substituents selected from the substituents exemplified above.

[0045] In this specification, "in cases where no substituent is indicated in the chemical formula or compound structure" means that a hydrogen atom is bonded to a carbon atom. However, due to deuterium ( 2 H is an isotope of hydrogen, therefore some hydrogen atoms can be deuterium.

[0046] In one embodiment of this application, "in the case where no substituent is indicated in the chemical formula or compound structure" may mean that all positions that can be substituents can be hydrogen or deuterium. In other words, since deuterium is an isotope of hydrogen, some hydrogen atoms may be deuterium as an isotope, and in this document, the deuterium content may be between 0% and 100%.

[0047] In one embodiment of this application, in the case where "no substituents are indicated in the chemical formula or compound structure", hydrogen and deuterium may be mixed in the compound when deuterium is not explicitly excluded (e.g., the deuterium content is 0%, the hydrogen content is 100%, or all substituents are hydrogen).

[0048] In one embodiment of this application, deuterium is an isotope of hydrogen, an element having a deuterium nucleus formed by one proton and one neutron, and can be represented as hydrogen-2, and its element symbol can also be written as D or 2 H.

[0049] In one embodiment of this application, an isotope refers to an atom having the same number of atoms (Z) but different mass numbers (A), and can also be interpreted as an element having the same number of protons but different numbers of neutrons.

[0050] In one embodiment of this application, when the total number of substituents that a basic compound may have is defined as T1, and the number of a specific substituent is defined as T2, the meaning of the content of a specific substituent T% can be defined as T2 / T1×100=T.

[0051] In other words, in one instance, in the case of... The statement that a phenyl group has a deuterium content of 20% means that the total number of substituents that the phenyl group may have is 5 (T1 in the formula), and the number of deuterium substituents is 1 (T2 in the formula). In other words, a phenyl group having a deuterium content of 20% can be represented by the following structural formula.

[0052]

[0053] Additionally, in one embodiment of this application, "phenyl with a deuterium content of 0%" may mean a phenyl that does not contain deuterium atoms, i.e., a phenyl with 5 hydrogen atoms.

[0054] In this specification, alkyl groups include straight-chain or branched alkyl groups and may be further substituted with other substituents. The number of carbon atoms in an alkyl group may be between 1 and 60, specifically between 1 and 40, and more specifically between 1 and 20. Specific examples of alkyl groups may include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tributyl, dibutyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tripentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, octyl, n-octyl, trioctyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like.

[0055] In this specification, alkenyl groups include straight-chain or branched alkenyl groups, and may be further substituted with other substituents. The number of carbon atoms in an alkenyl group may be between 2 and 60, specifically between 2 and 40, and more specifically between 2 and 20. Specific examples of alkenyl groups may include, but are not limited to, 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, stilbenyl group, styryl, and the like.

[0056] In this specification, the alkynyl group includes straight-chain or branched alkynyl groups and may be further substituted with other substituents. The number of carbon atoms in the alkynyl group can be between 2 and 60, specifically between 2 and 40, and more specifically between 2 and 20.

[0057] In this specification, cycloalkyl groups include monocyclic or polycyclic groups and may be further substituted with other substituents. Polycyclic here means a group in which the cycloalkyl group is directly linked to or fused with other cyclic groups. Other cyclic groups may be cycloalkyl groups, but may also be different types of cyclic groups such as heterocycloalkyl, aryl, and heteroaryl. The number of carbon atoms in a cycloalkyl group may be between 3 and 60, specifically between 3 and 40, and more specifically between 5 and 20. Specific examples of cycloalkyl groups may include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like.

[0058] In this specification, heterocyclic alkyl groups contain O, S, Se, N, or Si as heteroatoms, and may be monocyclic or polycyclic, and may be further substituted with other substituents. Polycyclic here means a group in which the heterocyclic alkyl group is directly linked to or fused with other cyclic groups. Other cyclic groups may be heterocyclic alkyl groups, but may also be different types of cyclic groups such as cycloalkyl, aryl, and heteroaryl. The number of carbon atoms in a heterocyclic alkyl group may be between 2 and 60, specifically between 2 and 40, and more specifically between 3 and 20.

[0059] In this specification, aryl groups include monocyclic or polycyclic groups and may be further substituted with other substituents. Polycyclic here means a group in which the aryl group is directly linked to or fused with other cyclic groups. Other cyclic groups may be aryl, but may also be different types of cyclic groups such as cycloalkyl, heterocycloalkyl, and heteroaryl. Aryl groups include spirocyclic groups. The number of carbon atoms in an aryl group may be between 6 and 60, specifically between 6 and 40, and more specifically between 6 and 25. When the aryl group is bicyclic or higher, the number of carbon atoms may be between 8 and 60, between 8 and 40, or between 8 and 30. Specific examples of aryl groups may include phenyl, biphenyl, terphenyl, naphthyl, anthracene, etc. alkyl, phenanthrene, perylene, fluoranthracene, dithionyl, fenyl, pyrene, anthracene, fused tetraphenyl, fused pentaphenyl, fluorenyl, indene, acenaphthene, benzo[a]fluorenyl, spirodifluorenyl, 2,3-dihydro-1H-indene, their fused cyclic groups and analogs, but not limited thereto.

[0060] In this specification, the fluorene group may be substituted, and adjacent substituents may bond to each other to form a ring.

[0061] When the fluorene group is substituted, the following structures may be included; however, the structures are not limited to these.

[0062]

[0063] In this specification, terphenyl includes straight-chain or branched chains and can be represented by the following structures.

[0064]

[0065] In this specification, heteroaryl groups include O, S, SO2, Se, N, or Si as heteroatoms, and may be monocyclic or polycyclic, and may be further substituted with other substituents. Polycyclic here means a group in which the heteroaryl group is directly linked or fused with other cyclic groups. Other cyclic groups may be heteroaryl, but may also be different types of cyclic groups such as cycloalkyl, heterocycloalkyl, and aryl. The number of carbon atoms in a heteroaryl group may be between 2 and 60, specifically between 2 and 40, and more specifically between 3 and 25. When the heteroaryl group is bicyclic or higher, the number of carbon atoms may be between 4 and 60, 4 and 40, or 4 and 25.Specific examples of heteroaryl groups may include pyridyl, pyrroloyl, pyrimidinyl, pyridazinyl, furanyl, thiopheneyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, furazolyl, oxadiazolyl, thiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiaranyl, diazinyl, oxazinyl, thiazolyl, and dioxinyl. (group), triazinyl, tetraazinyl, quinolinyl, isoquinolinyl, quinazolinyl, isoquinazolinyl, quinoxolinyl, naphridyl, acridineyl, phenanthridineyl, imidazopyridyl, diazanaphthyl, triazaindyl, indoleyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, benzothiophene, benzofuranyl, dibenzothiophene, dibenzofuranyl, carbazole, benzocarbazole, dibenzocarbazole, phenazinyl, dibenzothiophene, dibenzothiophene, dibenzothiophene, dibenzothiophene, dibenzothiophene, dibenzothiophene, dibenzothiophene group), spirocyclic di(dibenzothiol)yl, dihydrophenazinyl, phenoxazinyl, phenanthridine, indolo[2,3-a]carbazole, indolo[2,3-b]carbazole, indolinyl, 10,11-dihydro-dibenzo[b,f]azolinyl, 9,10-dihydroacridyl, phenazinyl, phenanthridine, terazinyl, naphridyl, phenolinyl, benzo[c][1,2,5]thiadiazolyl, 5,10-dihydrodibenzo[b,e][1,4]azasilolinyl, pyrazolo[1,5-c Quinazolinyl, pyrido[1,2-b]inzolyl, pyrido[1,2-a]imidazo[1,2-e]indolyl, benzofurano[2,3-d]pyrimidinyl; benzothieno[2,3-d]pyrimidinyl; benzofurano[2,3-a]carbazole, benzothieno[2,3-a]carbazole, 1,3-dihydroindolo[2,3-a]carbazole, benzofurano[3,2-a]carbazole, benzothieno[3,2-a]carbazole, 1,3-dihydroindolo[3, 2-a]carbazolyl, benzofurano[2,3-b]carbazolyl, benzothiopheno[2,3-b]carbazolyl, 1,3-dihydroindolo[2,3-b]carbazolyl, benzofurano[3,2-b]carbazolyl, benzothiopheno[3,2-b]carbazolyl, 1,3-dihydroindolo[3,2-b]carbazolyl, benzofurano[2,3-c]carbazolyl, benzothiopheno[2,3-c]carbazolyl, 1,3-dihydroindolo[2,3-c]carbazolyl, benzofurano[3, [2-c]carbazolyl, benzothio[3,2-c]carbazolyl, 1,3-dihydroindolo[3,2-c]carbazolyl, 1,3-dihydroindo[2,1-b]carbazolyl, 5,11-dihydroindo[1,2-b]carbazolyl, 5,12-dihydroindo[1,2-c]carbazolyl, 5,8-dihydroindo[2,1-c]carbazolyl, 7,12-dihydroindo[1,2-a]carbazolyl, 11,12-dihydroindo[2,1-a]carbazolyl and analogues, but not limited thereto.

[0066] In this specification, silane is a substituent comprising Si and having Si atoms directly linked as a free radical, and is represented by -Si(R101)(R102)(R103). R101 to R103 may be the same as or different from each other, and may each be independently a substituent formed from at least one of hydrogen; deuterium; halogen; alkyl; alkenyl; alkoxy; cycloalkyl; heterocycloalkyl; aryl; and heteroaryl. Specific examples of silane may include, but are not limited to, the structures described below.

[0067]

[0068] In this specification, the amino group is represented by -N(R104)(R105), and R104 and R105 may be the same as or different from each other, and may each be independently a substituent formed from at least one of hydrogen; deuterium; halogen group; alkyl; alkenyl; alkoxy; cycloalkyl; heterocycloalkyl; aryl; and heteroaryl. The amino group may be selected from the group consisting of -NH2; monoalkylamino; monoarylamino; monoheteroarylamino; dialkylamino; diarylamino; diheteroarylamino; alkylarylamino; alkylheteroarylamino; and arylheteroarylamino, and although not particularly limited thereto, the number of carbon atoms is preferably between 1 and 30. Specific examples of amino groups may include, but are not limited to, methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, naphthylamino, biphenylamino, diphenylamino, anthraceneamino, 9-methyl-anthraylamino, diphenylamino, phenylnaphthylamino, xylylamino, phenyltolylamino, triphenylamino, biphenylnaphthylamino, phenylbiphenylamino, biphenylfluorenylamino, phenyldiphenyltriphenylamino, biphenyldiphenyltriphenylamino, and the like.

[0069] In this specification, phosphine oxide is represented by -P(=O)(R106)(R107), and R106 and R107 may be the same as or different from each other, and may each be independently a substituent formed from at least one of hydrogen; deuterium; halogen group; alkyl; alkenyl; alkoxy; cycloalkyl; heterocycloalkyl; aryl; and heteroaryl. Specifically, phosphine oxide may be substituted with alkyl or aryl groups, and the examples described above may be used as alkyl and aryl groups. Examples of phosphine oxide may include, but are not limited to, dimethylphosphine oxide, diphenylphosphine oxide, dinaphthylphosphine oxide, and the like.

[0070] In this specification, except that arylene is a divalent group, the above description of aryl groups can be applied to arylene groups.

[0071] In this specification, the phenylene oxide may be selected from the following structures and may be further substituted with deuterium.

[0072]

[0073] In this specification, except that heteroaryl is a divalent group, the above description of heteroaryl can be applied to heteroaryl.

[0074] One embodiment of this specification provides a heterocyclic compound of formula 1.

[0075] In one embodiment of this specification, R1 to R10 may be the same as or different from each other, and each is independently hydrogen; deuterium; halogen group; cyano group; -Si(R11)(R12)(R13); -N(R14)(R15); substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl, and each of R11 to R15 is independently hydrogen; deuterium; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl.

[0076] In one embodiment of this specification, R1 to R10 may be the same as or different from each other, and each is independently hydrogen; deuterium; -N(R14)(R15); or substituted or unsubstituted C6 to C60 aryl, and R14 and R15 are each independently substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl.

[0077] In one embodiment of this specification, R1 to R10 may be the same as or different from each other, and each is independently hydrogen; deuterium; -N(R14)(R15); or substituted or unsubstituted C6 to C30 aryl groups, and R14 and R15 are each independently substituted or unsubstituted C6 to C30 aryl groups; or substituted or unsubstituted C2 to C30 heteroaryl groups.

[0078] In one embodiment of this specification, R1 to R10 may be the same as or different from each other, and each is independently hydrogen; deuterium; -N(R14)(R15); or substituted or unsubstituted C6 to C20 aryl groups, and R14 and R15 are each independently substituted or unsubstituted C6 to C20 aryl groups; or substituted or unsubstituted C2 to C20 heteroaryl groups.

[0079] In one embodiment of this specification, R1 to R10 may be the same as or different from each other, and each is independently hydrogen; deuterium; -N(R14)(R15); or substituted or unsubstituted C6 to C20 aryl groups, and R14 and R15 are each independently substituted or unsubstituted C6 to C20 tricyclic or lower ring aryl groups; or substituted or unsubstituted C2 to C20 heteroaryl groups containing O or S.

[0080] In one embodiment of this specification, at least one of R1 to R10 is -(L)lN(R24)(R25), and at least one of the remaining portions of R1 to R10 is a substituted or unsubstituted C6 to C60 aryl group.

[0081] In one embodiment of this specification, at least one of R1 to R10 is -(L)lN(R24)(R25), and at least one of the remaining portions of R1 to R10 is a substituted or unsubstituted C6 to C30 aryl group.

[0082] In one embodiment of this specification, at least one of R1 to R10 is -(L)lN(R24)(R25), and at least one of the remaining portions of R1 to R10 is a substituted or unsubstituted C6 to C20 aryl group.

[0083] In one embodiment of this specification, at least one of R1 to R10 is -(L)lN(R24)(R25), and at least one of the remaining portions of R1 to R10 may be a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted terphenyl; a substituted or unsubstituted naphthyl; a substituted or unsubstituted phenanthyl; a substituted or unsubstituted pyrene; or a substituted or unsubstituted triphenylene.

[0084] In one embodiment of this specification, at least one of R1 to R10 is -(L)lN(R24)(R25), and at least one of the remaining portions of R1 to R10 is an unsubstituted or deuterated C6 to C60 aryl group.

[0085] In one embodiment of this specification, at least one of R1 to R10 is -(L)lN(R24)(R25), and at least one of the remaining portions of R1 to R10 is an unsubstituted or deuterated C6 to C30 aryl group.

[0086] In one embodiment of this specification, at least one of R1 to R10 is -(L)lN(R24)(R25), and at least one of the remaining portions of R1 to R10 is an unsubstituted or deuterated C6 to C20 aryl group.

[0087] In one embodiment of this specification, at least one of R1 to R10 is -(L)lN(R24)(R25), and at least one of the remaining portions of R1 to R10 may be an unsubstituted or deuterated phenyl; an unsubstituted or deuterated biphenyl; an unsubstituted or deuterated terphenyl; an unsubstituted or deuterated naphthyl; an unsubstituted or deuterated phenanthyl; an unsubstituted or deuterated pyrene; or an unsubstituted or deuterated triphenylene.

[0088] In one embodiment of this specification, at least one of R1 to R10 is -(L)lN(R24)(R25), and R24 and R25 are the same as or different from each other, and each is independently a substituted or unsubstituted C6 to C60 aryl; or a substituted or unsubstituted C2 to C60 heteroaryl.

[0089] In one embodiment of this specification, at least one of R1 to R10 is -(L)lN(R24)(R25), and R24 and R25 may be the same as or different from each other, and each is independently a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0090] In one embodiment of this specification, at least one of R1 to R10 is -(L)lN(R24)(R25), and R24 and R25 may be the same as or different from each other, and each is independently a substituted or unsubstituted C6 to C20 aryl; or a substituted or unsubstituted C2 to C20 heteroaryl.

[0091] In one embodiment of this specification, at least one of R1 to R10 is -(L)lN(R24)(R25), and R24 and R25 may be the same as or different from each other, and each is independently a substituted or unsubstituted C6 to C20 tricyclic or lower ring aryl; a substituted or unsubstituted C2 to C20 heteroaryl containing O or S; or a substituted or unsubstituted C2 to C20 heteroaryl containing C=N bonds.

[0092] In one embodiment of this specification, at least one of R1 to R10 is -(L)lN(R24)(R25), and R24 and R25 may be the same as or different from each other, and each is independently a substituted or unsubstituted C6 to C20 tricyclic or lower ring aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group containing O or S.

[0093] In one embodiment of this specification, at least one of R1 to R10 is -(L)lN(R24)(R25), and R24 and R25 may be the same as or different from each other, and may each be independently a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted terphenyl; a substituted or unsubstituted naphthyl; a substituted or unsubstituted phenanthyl; a substituted or unsubstituted fluorenyl; a substituted or unsubstituted dibenzofuranyl; or a substituted or unsubstituted dibenzothiopheneyl.

[0094] In one embodiment of this specification, at least one of R1 to R10 is -(L)lN(R24)(R25), and R24 and R25 may be the same as or different from each other, and may each be independently an unsubstituted or deuterated phenyl; an unsubstituted or deuterated biphenyl; an unsubstituted or deuterated terphenyl; an unsubstituted or deuterated naphthyl; an unsubstituted or deuterated phenanthyl; an unsubstituted or deuterated fluorenyl or substituted with one or more substituents selected from deuterium, alkyl and unsubstituted or deuterated aryl; an unsubstituted or deuterated dibenzofuranyl or substituted with one or more substituents selected from deuterium and aryl; or an unsubstituted or deuterated dibenzothiophenyl.

[0095] In one embodiment of this specification, at least one of R1 to R10 is -(L)lN(R24)(R25), and R24 and R25 may be the same as or different from each other, and may each be independently an unsubstituted or deuterated phenyl; an unsubstituted or deuterated biphenyl; an unsubstituted or deuterated terphenyl; an unsubstituted or deuterated naphthyl; an unsubstituted or deuterated phenanthyl; an unsubstituted or deuterated fluorenyl or substituted with one or more substituents selected from deuterium, alkyl and aryl; an unsubstituted or deuterated dibenzofuranyl or substituted with one or more substituents selected from deuterium and aryl; or an unsubstituted or deuterated dibenzothiopheneyl or substituted with one or more substituents selected from deuterium and aryl.

[0096] In one embodiment of this specification, at least one of R24 and R25 may be a substituted or unsubstituted C10 to C20 tricyclic or lower ring aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group containing O or S.

[0097] In one embodiment of this specification, at least one of R24 and R25 may be a substituted or unsubstituted biphenyl; a substituted or unsubstituted terphenyl; a substituted or unsubstituted naphthyl; a substituted or unsubstituted phenanthyl; a substituted or unsubstituted fluorenyl; a substituted or unsubstituted dibenzofuranyl; or a substituted or unsubstituted dibenzothiopheneyl.

[0098] In one embodiment of this specification, -(L)lN(R24)(R25) may be represented by any of the following chemical formulas N-1 to N-3.

[0099] [Chemical formula N-1]

[0100]

[0101] [Chemical formula N-2]

[0102]

[0103] [Chemical formula N-3]

[0104]

[0105] In chemical formulas N-1 to N-3,

[0106] L and l have the same definitions as in chemical formula 1.

[0107] X and Y are each independently O; or S,

[0108] Ar1 and Ar2 may be identical or different from each other, and each is independently a substituted or unsubstituted C6 to C60 aryl group.

[0109] R31 and R32 are each independently hydrogen; deuterium; or substituted or unsubstituted C6 to C30 aryl groups, and

[0110] r31 and r32 are each integers from 0 to 7, and when r31 and r32 are each 2 or greater than 2, the substituents in parentheses are the same or different from each other.

[0111] In one embodiment of this specification, L is a direct bond; a substituted or unsubstituted C6 to C60 arylene; or a substituted or unsubstituted C2 to C60 heteroarylene.

[0112] In one embodiment of this specification, L is a direct bond; or a substituted or unsubstituted C6 to C60 arylene.

[0113] In one embodiment of this specification, L is a direct bond; or a substituted or unsubstituted C6 to C30 arylene.

[0114] In one embodiment of this specification, L is a direct bond; or a substituted or unsubstituted C6 to C15 arylene group.

[0115] In one embodiment of this specification, L may be a direct bond; or a substituted or unsubstituted phenylene oxide.

[0116] In one embodiment of this specification, L may be a direct bond; or an unsubstituted or deuterated phenylene.

[0117] In one embodiment of this specification, l is an integer from 1 to 3.

[0118] In one embodiment of this specification, l may be 1.

[0119] In one embodiment of this specification, Ar1 and Ar2 in chemical formula N-1 may be the same as or different from each other, and each is independently a substituted or unsubstituted C6 to C60 aryl group.

[0120] In one embodiment of this specification, Ar1 and Ar2 in chemical formula N-1 may be the same as or different from each other, and each is independently a substituted or unsubstituted C6 to C30 aryl group.

[0121] In one embodiment of this specification, Ar1 and Ar2 in chemical formula N-1 may be the same as or different from each other, and each is independently a substituted or unsubstituted C6 to C20 aryl group.

[0122] In one embodiment of this specification, Ar1 and Ar2 in chemical formula N-1 may be the same as or different from each other, and may each be independently a substituted or unsubstituted C6 to C20 tricyclic or lower ring aryl group.

[0123] In one embodiment of this specification, Ar1 and Ar2 in formula N-1 may be the same as or different from each other, and may each be independently a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted terphenyl; a substituted or unsubstituted naphthyl; a substituted or unsubstituted phenanthryl; or a substituted or unsubstituted fluorenyl.

[0124] In one embodiment of this specification, Ar1 and Ar2 in formula N-1 may be the same as or different from each other, and may each be independently an unsubstituted or deuterated phenyl; an unsubstituted or deuterated biphenyl; an unsubstituted or deuterated terphenyl; an unsubstituted or deuterated naphthyl; an unsubstituted or deuterated phenanthryl; or an unsubstituted or deuterated fluorenyl substituted with one or more substituents selected from deuterium, alkyl and unsubstituted or deuterated aryl.

[0125] In one embodiment of this specification, Ar1 and Ar2 in formula N-1 may be the same as or different from each other, and may each be independently an unsubstituted or deuterated phenyl; an unsubstituted or deuterated biphenyl; an unsubstituted or deuterated terphenyl; an unsubstituted or deuterated naphthyl; an unsubstituted or deuterated phenanthryl; or an unsubstituted or fluorenyl substituted with one or more substituents selected from deuterium, alkyl and aryl.

[0126] In one embodiment of this specification, Ar2 in chemical formula N-1 may be a substituted or unsubstituted C10 to C20 tricyclic or lower ring aryl group.

[0127] In one embodiment of this specification, Ar2 in chemical formula N-1 may be an unsubstituted or deuterated biphenyl; an unsubstituted or deuterated terphenyl; an unsubstituted or deuterated naphthyl; an unsubstituted or deuterated phenanthryl; or an unsubstituted or deuterated fluorenyl group substituted with one or more substituents selected from deuterium, alkyl, and unsubstituted or deuterated aryl groups.

[0128] In one embodiment of this specification, Ar2 in chemical formula N-1 may be an unsubstituted or deuterated biphenyl; an unsubstituted or deuterated terphenyl; an unsubstituted or deuterated naphthyl; an unsubstituted or deuterated phenanthryl; or an unsubstituted or deuterated fluorenyl or fluorenyl selected from deuterium, alkyl and aryl.

[0129] In one embodiment of this specification, the description of Ar1 in chemical formula N-2 is the same as the description of Ar1 in chemical formula N-1.

[0130] In one embodiment of this specification, R31 in chemical formula N-2 is hydrogen; deuterium; or a substituted or unsubstituted C6 to C30 aryl group.

[0131] In one embodiment of this specification, R31 in chemical formula N-2 is hydrogen; deuterium; or a substituted or unsubstituted phenyl.

[0132] In one embodiment of this specification, R31 in chemical formula N-2 is hydrogen; deuterium; or an unsubstituted or deuterated phenyl group.

[0133] In one embodiment of this specification, the description of R31 in chemical formula N-3 is the same as the description of R31 in chemical formula N-2.

[0134] In one embodiment of this specification, R32 in chemical formula N-3 is hydrogen; deuterium; or a substituted or unsubstituted C6 to C30 aryl group.

[0135] In one embodiment of this specification, R32 in chemical formula N-3 is hydrogen; deuterium; or a substituted or unsubstituted phenyl.

[0136] In one embodiment of this specification, R32 in chemical formula N-3 is hydrogen; deuterium; or an unsubstituted or deuterated phenyl group.

[0137] In one embodiment of this specification, X and Y in chemical formulas N-2 and N-3 are each independently O; or S.

[0138] In one embodiment of this specification, X and Y in chemical formulas N-2 and N-3 are different from each other.

[0139] In one embodiment of this specification, when X is O in the chemical formula N-3, Y is S.

[0140] In one embodiment of this specification, when X is S in chemical formula N-3, Y is O.

[0141] In one embodiment of this specification, any one of R1 to R10 is -(L)lN(R24)(R25), the other one of R1 to R10 is a C6 to C60 aryl group that is unsubstituted or substituted with one or more substituents selected from deuterium, alkyl and unsubstituted or deuterated aryl groups, and the remainder of R1 to R10 is hydrogen; or deuterium.

[0142] In one embodiment of this specification, any one of R1 to R10 is -(L)lN(R24)(R25), the other one of R1 to R10 is a C6 to C30 aryl group that is unsubstituted or substituted with one or more substituents selected from deuterium, alkyl and unsubstituted or deuterium-substituted aryl groups, and the remainder of R1 to R10 is hydrogen; or deuterium.

[0143] In one embodiment of this specification, any one of R1 to R10 is -(L)lN(R24)(R25), the other one of R1 to R10 is an unsubstituted or deuterated C6 to C60 aryl group, and the remainder of R1 to R10 is hydrogen; or deuterium.

[0144] In one embodiment of this specification, any one of R1 to R10 is -(L)lN(R24)(R25), the other one of R1 to R10 is an unsubstituted or deuterated C6 to C30 aryl group, and the remainder of R1 to R10 is hydrogen; or deuterium.

[0145] In one embodiment of this specification, any one of R1 to R10 is -(L)lN(R24)(R25), the other one of R1 to R10 is an unsubstituted or deuterated C6 to C20 aryl group, and the remainder of R1 to R10 is hydrogen; or deuterium.

[0146] In one embodiment of this specification, chemical formula 1 may be represented by any of the following chemical formulas 1-1 to 1-4.

[0147] [Chemical Formula 1-1]

[0148]

[0149] [Chemical Formula 1-2]

[0150]

[0151] [Chemical Formulas 1-3]

[0152]

[0153] [Chemical Formulas 1-4]

[0154]

[0155] In chemical formulas 1-1 to 1-4,

[0156] L, l, R24, and R25 have the same definitions as in chemical formula 1.

[0157] Ar is a substituted or unsubstituted C6 to C60 aryl group.

[0158] R41 and R42 are each independently hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0159] r41 is an integer from 0 to 3, r42 is an integer from 0 to 5, r43 is an integer from 0 to 2, r44 is an integer from 0 to 6, and r45 and r46 are each integers from 0 to 4.

[0160] When r41, r42, and r44 to r46 are 2 or greater than 2, or when r43 is 2, the substituents in parentheses are the same or different from each other.

[0161] In one embodiment of this specification, Ar is a substituted or unsubstituted C6 to C60 aryl group.

[0162] In one embodiment of this specification, Ar is a substituted or unsubstituted C6 to C30 aryl group.

[0163] In one embodiment of this specification, Ar is a substituted or unsubstituted C6 to C20 aryl group.

[0164] In one embodiment of this specification, Ar may be a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted terphenyl; a substituted or unsubstituted naphthyl; a substituted or unsubstituted phenanthyl; a substituted or unsubstituted pyrene; or a substituted or unsubstituted triphenylene.

[0165] In one embodiment of this specification, Ar is an unsubstituted or deuterated C6 to C60 aryl group.

[0166] In one embodiment of this specification, Ar is an unsubstituted or deuterated C6 to C30 aryl group.

[0167] In one embodiment of this specification, Ar is an unsubstituted or deuterated C6 to C20 aryl group.

[0168] In one embodiment of this specification, Ar may be an unsubstituted or deuterated phenyl; an unsubstituted or deuterated biphenyl; an unsubstituted or deuterated terphenyl; an unsubstituted or deuterated naphthyl; an unsubstituted or deuterated phenanthryl; an unsubstituted or deuterated pyrene; or an unsubstituted or deuterated triphenylene.

[0169] In one embodiment of this specification, R41 and R42 are each independently hydrogen; deuterium; a substituted or unsubstituted C1 to C30 alkyl; a substituted or unsubstituted C3 to C30 cycloalkyl; a substituted or unsubstituted C2 to C30 heterocycloalkyl; a substituted or unsubstituted C6 to C30 aryl; or a substituted or unsubstituted C2 to C30 heteroaryl.

[0170] In one embodiment of this specification, R41 and R42 are each independently hydrogen; deuterium; substituted or unsubstituted C6 to C30 aryl; or substituted or unsubstituted C2 to C30 heteroaryl.

[0171] In one embodiment of this specification, R41 and R42 are each independently hydrogen; deuterium; substituted or unsubstituted C6 to C20 aryl; or substituted or unsubstituted C2 to C20 heteroaryl.

[0172] In one embodiment of this specification, R41 and R42 are each independently hydrogen; or deuterium.

[0173] In one embodiment of this specification, chemical formula 1 may be represented by chemical formula 1-1.

[0174] In one embodiment of this specification, chemical formula 1 may be represented by chemical formulas 1-2.

[0175] In one embodiment of this specification, chemical formula 1 may be represented by chemical formulas 1-3.

[0176] In one embodiment of this specification, chemical formula 1 may be represented by chemical formulas 1-4.

[0177] In one embodiment of this specification, R1 is -(L)lN(R24)(R25), and R2 is a substituted or unsubstituted C6 to C60 aryl group.

[0178] In one embodiment of this specification, R1 is -(L)lN(R24)(R25), and R3 is a substituted or unsubstituted C6 to C60 aryl group.

[0179] In one embodiment of this specification, R1 is -(L)lN(R24)(R25), and R4 is a substituted or unsubstituted C6 to C60 aryl group.

[0180] In one embodiment of this specification, R1 is -(L)lN(R24)(R25), and R5 is a substituted or unsubstituted C6 to C60 aryl group.

[0181] In one embodiment of this specification, R1 is -(L)lN(R24)(R25), and R6 is a substituted or unsubstituted C6 to C60 aryl group.

[0182] In one embodiment of this specification, R1 is -(L)lN(R24)(R25), and R7 is a substituted or unsubstituted C6 to C60 aryl group.

[0183] In one embodiment of this specification, R1 is -(L)lN(R24)(R25), and R8 is a substituted or unsubstituted C6 to C60 aryl group.

[0184] In one embodiment of this specification, R1 is -(L)lN(R24)(R25), and R9 is a substituted or unsubstituted C6 to C60 aryl group.

[0185] In one embodiment of this specification, R1 is -(L)lN(R24)(R25), and R10 is a substituted or unsubstituted C6 to C60 aryl group.

[0186] In one embodiment of this specification, R2 is -(L)lN(R24)(R25), and R1 is a substituted or unsubstituted C6 to C60 aryl group.

[0187] In one embodiment of this specification, R2 is -(L)lN(R24)(R25), and R3 is a substituted or unsubstituted C6 to C60 aryl group.

[0188] In one embodiment of this specification, R2 is -(L)lN(R24)(R25), and R4 is a substituted or unsubstituted C6 to C60 aryl group.

[0189] In one embodiment of this specification, R2 is -(L)lN(R24)(R25), and R5 is a substituted or unsubstituted C6 to C60 aryl group.

[0190] In one embodiment of this specification, R2 is -(L)lN(R24)(R25), and R6 is a substituted or unsubstituted C6 to C60 aryl group.

[0191] In one embodiment of this specification, R2 is -(L)lN(R24)(R25), and R7 is a substituted or unsubstituted C6 to C60 aryl group.

[0192] In one embodiment of this specification, R2 is -(L)lN(R24)(R25), and R8 is a substituted or unsubstituted C6 to C60 aryl group.

[0193] In one embodiment of this specification, R2 is -(L)lN(R24)(R25), and R9 is a substituted or unsubstituted C6 to C60 aryl group.

[0194] In one embodiment of this specification, R2 is -(L)lN(R24)(R25), and R10 is a substituted or unsubstituted C6 to C60 aryl group.

[0195] In one embodiment of this specification, R3 is -(L)lN(R24)(R25), and R1 is a substituted or unsubstituted C6 to C60 aryl group.

[0196] In one embodiment of this specification, R3 is -(L)lN(R24)(R25), and R2 is a substituted or unsubstituted C6 to C60 aryl group.

[0197] In one embodiment of this specification, R3 is -(L)lN(R24)(R25), and R4 is a substituted or unsubstituted C6 to C60 aryl group.

[0198] In one embodiment of this specification, R3 is -(L)lN(R24)(R25), and R5 is a substituted or unsubstituted C6 to C60 aryl group.

[0199] In one embodiment of this specification, R3 is -(L)lN(R24)(R25), and R6 is a substituted or unsubstituted C6 to C60 aryl group.

[0200] In one embodiment of this specification, R3 is -(L)lN(R24)(R25), and R7 is a substituted or unsubstituted C6 to C60 aryl group.

[0201] In one embodiment of this specification, R3 is -(L)lN(R24)(R25), and R8 is a substituted or unsubstituted C6 to C60 aryl group.

[0202] In one embodiment of this specification, R3 is -(L)lN(R24)(R25), and R9 is a substituted or unsubstituted C6 to C60 aryl group.

[0203] In one embodiment of this specification, R3 is -(L)lN(R24)(R25), and R10 is a substituted or unsubstituted C6 to C60 aryl group.

[0204] In one embodiment of this specification, R4 is -(L)lN(R24)(R25), and R1 is a substituted or unsubstituted C6 to C60 aryl group.

[0205] In one embodiment of this specification, R4 is -(L)lN(R24)(R25), and R2 is a substituted or unsubstituted C6 to C60 aryl group.

[0206] In one embodiment of this specification, R4 is -(L)lN(R24)(R25), and R3 is a substituted or unsubstituted C6 to C60 aryl group.

[0207] In one embodiment of this specification, R4 is -(L)lN(R24)(R25), and R5 is a substituted or unsubstituted C6 to C60 aryl group.

[0208] In one embodiment of this specification, R4 is -(L)lN(R24)(R25), and R6 is a substituted or unsubstituted C6 to C60 aryl group.

[0209] In one embodiment of this specification, R4 is -(L)lN(R24)(R25), and R7 is a substituted or unsubstituted C6 to C60 aryl group.

[0210] In one embodiment of this specification, R4 is -(L)lN(R24)(R25), and R8 is a substituted or unsubstituted C6 to C60 aryl group.

[0211] In one embodiment of this specification, R4 is -(L)lN(R24)(R25), and R9 is a substituted or unsubstituted C6 to C60 aryl group.

[0212] In one embodiment of this specification, R4 is -(L)lN(R24)(R25), and R10 is a substituted or unsubstituted C6 to C60 aryl group.

[0213] In one embodiment of this specification, R5 is -(L)lN(R24)(R25), and R1 is a substituted or unsubstituted C6 to C60 aryl group.

[0214] In one embodiment of this specification, R5 is -(L)lN(R24)(R25), and R2 is a substituted or unsubstituted C6 to C60 aryl group.

[0215] In one embodiment of this specification, R5 is -(L)lN(R24)(R25), and R3 is a substituted or unsubstituted C6 to C60 aryl group.

[0216] In one embodiment of this specification, R5 is -(L)lN(R24)(R25), and R4 is a substituted or unsubstituted C6 to C60 aryl group.

[0217] In one embodiment of this specification, R5 is -(L)lN(R24)(R25), and R6 is a substituted or unsubstituted C6 to C60 aryl group.

[0218] In one embodiment of this specification, R5 is -(L)lN(R24)(R25), and R7 is a substituted or unsubstituted C6 to C60 aryl group.

[0219] In one embodiment of this specification, R5 is -(L)lN(R24)(R25), and R8 is a substituted or unsubstituted C6 to C60 aryl group.

[0220] In one embodiment of this specification, R5 is -(L)lN(R24)(R25), and R9 is a substituted or unsubstituted C6 to C60 aryl group.

[0221] In one embodiment of this specification, R5 is -(L)lN(R24)(R25), and R10 is a substituted or unsubstituted C6 to C60 aryl group.

[0222] In one embodiment of this specification, R6 is -(L)lN(R24)(R25), and R1 is a substituted or unsubstituted C6 to C60 aryl group.

[0223] In one embodiment of this specification, R6 is -(L)lN(R24)(R25), and R2 is a substituted or unsubstituted C6 to C60 aryl group.

[0224] In one embodiment of this specification, R6 is -(L)lN(R24)(R25), and R3 is a substituted or unsubstituted C6 to C60 aryl group.

[0225] In one embodiment of this specification, R6 is -(L)lN(R24)(R25), and R4 is a substituted or unsubstituted C6 to C60 aryl group.

[0226] In one embodiment of this specification, R6 is -(L)lN(R24)(R25), and R5 is a substituted or unsubstituted C6 to C60 aryl group.

[0227] In one embodiment of this specification, R6 is -(L)lN(R24)(R25), and R7 is a substituted or unsubstituted C6 to C60 aryl group.

[0228] In one embodiment of this specification, R6 is -(L)lN(R24)(R25), and R8 is a substituted or unsubstituted C6 to C60 aryl group.

[0229] In one embodiment of this specification, R6 is -(L)lN(R24)(R25), and R9 is a substituted or unsubstituted C6 to C60 aryl group.

[0230] In one embodiment of this specification, R6 is -(L)lN(R24)(R25), and R10 is a substituted or unsubstituted C6 to C60 aryl group.

[0231] In one embodiment of this specification, R7 is -(L)lN(R24)(R25), and R1 is a substituted or unsubstituted C6 to C60 aryl group.

[0232] In one embodiment of this specification, R7 is -(L)lN(R24)(R25), and R2 is a substituted or unsubstituted C6 to C60 aryl group.

[0233] In one embodiment of this specification, R7 is -(L)lN(R24)(R25), and R3 is a substituted or unsubstituted C6 to C60 aryl group.

[0234] In one embodiment of this specification, R7 is -(L)lN(R24)(R25), and R4 is a substituted or unsubstituted C6 to C60 aryl group.

[0235] In one embodiment of this specification, R7 is -(L)lN(R24)(R25), and R5 is a substituted or unsubstituted C6 to C60 aryl group.

[0236] In one embodiment of this specification, R7 is -(L)lN(R24)(R25), and R6 is a substituted or unsubstituted C6 to C60 aryl group.

[0237] In one embodiment of this specification, R7 is -(L)lN(R24)(R25), and R8 is a substituted or unsubstituted C6 to C60 aryl group.

[0238] In one embodiment of this specification, R7 is -(L)lN(R24)(R25), and R9 is a substituted or unsubstituted C6 to C60 aryl group.

[0239] In one embodiment of this specification, R7 is -(L)lN(R24)(R25), and R10 is a substituted or unsubstituted C6 to C60 aryl group.

[0240] In one embodiment of this specification, R8 is -(L)lN(R24)(R25), and R1 is a substituted or unsubstituted C6 to C60 aryl group.

[0241] In one embodiment of this specification, R8 is -(L)lN(R24)(R25), and R2 is a substituted or unsubstituted C6 to C60 aryl group.

[0242] In one embodiment of this specification, R8 is -(L)lN(R24)(R25), and R3 is a substituted or unsubstituted C6 to C60 aryl group.

[0243] In one embodiment of this specification, R8 is -(L)lN(R24)(R25), and R4 is a substituted or unsubstituted C6 to C60 aryl group.

[0244] In one embodiment of this specification, R8 is -(L)lN(R24)(R25), and R5 is a substituted or unsubstituted C6 to C60 aryl group.

[0245] In one embodiment of this specification, R8 is -(L)lN(R24)(R25), and R6 is a substituted or unsubstituted C6 to C60 aryl group.

[0246] In one embodiment of this specification, R8 is -(L)lN(R24)(R25), and R7 is a substituted or unsubstituted C6 to C60 aryl group.

[0247] In one embodiment of this specification, R8 is -(L)lN(R24)(R25), and R9 is a substituted or unsubstituted C6 to C60 aryl group.

[0248] In one embodiment of this specification, R8 is -(L)lN(R24)(R25), and R10 is a substituted or unsubstituted C6 to C60 aryl group.

[0249] In one embodiment of this specification, R9 is -(L)lN(R24)(R25), and R1 is a substituted or unsubstituted C6 to C60 aryl group.

[0250] In one embodiment of this specification, R9 is -(L)lN(R24)(R25), and R2 is a substituted or unsubstituted C6 to C60 aryl group.

[0251] In one embodiment of this specification, R9 is -(L)lN(R24)(R25), and R3 is a substituted or unsubstituted C6 to C60 aryl group.

[0252] In one embodiment of this specification, R9 is -(L)lN(R24)(R25), and R4 is a substituted or unsubstituted C6 to C60 aryl group.

[0253] In one embodiment of this specification, R9 is -(L)lN(R24)(R25), and R5 is a substituted or unsubstituted C6 to C60 aryl group.

[0254] In one embodiment of this specification, R9 is -(L)lN(R24)(R25), and R6 is a substituted or unsubstituted C6 to C60 aryl group.

[0255] In one embodiment of this specification, R9 is -(L)lN(R24)(R25), and R7 is a substituted or unsubstituted C6 to C60 aryl group.

[0256] In one embodiment of this specification, R9 is -(L)lN(R24)(R25), and R8 is a substituted or unsubstituted C6 to C60 aryl group.

[0257] In one embodiment of this specification, R9 is -(L)lN(R24)(R25), and R10 is a substituted or unsubstituted C6 to C60 aryl group.

[0258] In one embodiment of this specification, R10 is -(L)lN(R24)(R25), and R1 is a substituted or unsubstituted C6 to C60 aryl group.

[0259] In one embodiment of this specification, R10 is -(L)lN(R24)(R25), and R2 is a substituted or unsubstituted C6 to C60 aryl group.

[0260] In one embodiment of this specification, R10 is -(L)lN(R24)(R25), and R3 is a substituted or unsubstituted C6 to C60 aryl group.

[0261] In one embodiment of this specification, R10 is -(L)lN(R24)(R25), and R4 is a substituted or unsubstituted C6 to C60 aryl group.

[0262] In one embodiment of this specification, R10 is -(L)lN(R24)(R25), and R5 is a substituted or unsubstituted C6 to C60 aryl group.

[0263] In one embodiment of this specification, R10 is -(L)lN(R24)(R25), and R6 is a substituted or unsubstituted C6 to C60 aryl group.

[0264] In one embodiment of this specification, R10 is -(L)lN(R24)(R25), and R7 is a substituted or unsubstituted C6 to C60 aryl group.

[0265] In one embodiment of this specification, R10 is -(L)lN(R24)(R25), and R8 is a substituted or unsubstituted C6 to C60 aryl group.

[0266] In one embodiment of this specification, R10 is -(L)lN(R24)(R25), and R9 is a substituted or unsubstituted C6 to C60 aryl group.

[0267] In one embodiment of this specification, chemical formula 1 may have a deuterium content of 0% to 100%.

[0268] In one embodiment of this specification, chemical formula 1 may have a deuterium content of 0%.

[0269] In one embodiment of this specification, chemical formula 1 may have a deuterium content greater than 0% and less than or equal to 100%.

[0270] In one embodiment of this specification, chemical formula 1 may have a deuterium content of 10% to 100%.

[0271] In one embodiment of this specification, Formula 1 may have a deuterium content of 20% to 100%, 30% to 100%, or 40% to 100%.

[0272] In one embodiment of this specification, Formula 1 may have a deuterium content of 0% or 10% to 100%.

[0273] In one embodiment of this application, the deuterium content in the heterocyclic compound of Formula 1 meets the above range, and although the compounds without deuterium have almost similar photochemical properties to those containing deuterium, when deposited on a thin film, the deuterium-containing materials tend to stack with a narrower intermolecular distance.

[0274] Accordingly, when manufacturing electron-only devices (EOD) and hole-only devices (HOD) and examining voltage-dependent current densities, it was identified that, among the heterocyclic compounds of Formula 1 according to this application, compounds containing deuterium exhibit a much more balanced charge transfer property compared to compounds not containing deuterium.

[0275] In addition, when the surface of the thin film was examined using an atomic force microscope (AFM), it was found that the thin film made with deuterium-containing compounds was deposited as a more uniform surface without aggregated areas.

[0276] In addition, the single bond dissociation energy of carbon and deuterium is higher than that of carbon and hydrogen. When the deuterium content in the heterocyclic compound of chemical formula 1 according to this application meets the above range, the effect of improving the device lifetime is obtained by increasing the stability of the entire molecule.

[0277] In one embodiment of this specification, chemical formula 1 may be represented by any of the following compounds, but is not limited thereto.

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298] Furthermore, by introducing various substituents into the structure of Formula 1, compounds possessing the unique properties of the introduced substituents can be synthesized. For example, by introducing substituents commonly used as hole injection layer materials, hole transfer layer materials, light-emitting layer materials, electron transfer layer materials, and charge generation layer materials for manufacturing organic light-emitting elements into the core structure, materials that meet the requirements of each organic material layer can be synthesized.

[0299] Furthermore, by introducing various substituents into the structure of Formula 1, the energy band gap can be precisely controlled, while simultaneously enhancing the properties at the interface between organic materials, and the application of the materials can be diversified.

[0300] One embodiment of this specification provides an organic light-emitting element, the organic light-emitting element comprising: a first electrode; a second electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the multiple organic material layers comprise a heterocyclic compound of formula 1.

[0301] In one embodiment of this specification, the first electrode may be an anode and the second electrode may be a cathode.

[0302] In another embodiment of this specification, the first electrode may be a cathode, and the second electrode may be an anode.

[0303] In one embodiment of this specification, the organic light-emitting element may be a blue organic light-emitting element, and the heterocyclic compound of Formula 1 may be used as a material for the blue organic light-emitting element. For example, the heterocyclic compound of Formula 1 may be contained in the hole transfer layer or electron blocking layer of the blue organic light-emitting element.

[0304] In one embodiment of this specification, the organic light-emitting element may be a green organic light-emitting element, and the heterocyclic compound of Formula 1 may be used as a material for the green organic light-emitting element. For example, the heterocyclic compound of Formula 1 may be contained in the hole transfer layer or electron blocking layer of the green organic light-emitting element.

[0305] In one embodiment of this specification, the organic light-emitting element may be a red organic light-emitting element, and the heterocyclic compound of Formula 1 may be used as a material for the red organic light-emitting element. For example, the heterocyclic compound of Formula 1 may be contained in the hole transfer layer or electron blocking layer of the red organic light-emitting element.

[0306] In addition to using the aforementioned heterocyclic compounds to form one or more organic material layers, the organic light-emitting elements in this specification can be manufactured using commonly used organic light-emitting element manufacturing methods and materials.

[0307] When manufacturing organic light-emitting devices, solution coating and vacuum deposition methods can be used to form heterocyclic compounds into organic material layers. In this document, solution coating methods refer to, but are not limited to, spin coating, dip coating, inkjet printing, screen printing, spray method, roll coating, and similar methods.

[0308] The organic material layer of the organic light-emitting element described in this specification can be formed as a single-layer structure, but it can also be formed as a multilayer structure in which two or more organic material layers are stacked. For example, the organic light-emitting element disclosed herein may have a structure including a hole injection layer, a hole transfer layer, a light-emitting layer, an electron transfer layer, an electron injection layer, and the like as organic material layers. However, the structure of the organic light-emitting element is not limited to this, and may include fewer organic material layers.

[0309] In the organic light-emitting element of this specification, the organic material layer includes a hole transfer layer, and the hole transfer layer may contain a heterocyclic compound of formula 1.

[0310] In the organic light-emitting element of this specification, the organic material layer includes an electron blocking layer, and the electron blocking layer may contain a heterocyclic compound of formula 1.

[0311] The organic light-emitting element disclosed herein may further include one, two, or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transfer layer, an electron injection layer, an electron transfer layer, an electron blocking layer, and a hole blocking layer.

[0312] Figures 1 to 4 The diagram illustrates the stacking order of electrodes and organic material layers in an organic light-emitting element according to one embodiment of this specification. However, the scope of this application is not limited to these figures, and structures of organic light-emitting elements known in this art can also be used in this application.

[0313] Figure 1This illustrates an organic light-emitting element in which an anode 200, an organic material layer 300, and a cathode 400 are continuously stacked on a substrate 100. However, the structure is not limited to this one, and other structures are also possible. Figure 2 As shown, an organic light-emitting element in which the cathode, organic material layer and anode are continuously stacked on the substrate can also be obtained.

[0314] Figure 3 and Figure 4 This illustrates a case where the organic material layers are multiple. According to... Figure 3 The organic light-emitting element includes a hole injection layer 301, a hole transfer layer 302, a light-emitting layer 304, a hole blocking layer 305, an electron transfer layer 306, and an electron injection layer 307, and according to... Figure 4 The organic light-emitting element includes a hole injection layer 301, a hole transfer layer 302, an electron blocking layer 303, a light-emitting layer 304, an electron transfer layer 306, and an electron injection layer 307. However, the scope of this application is not limited to this stacked structure, and some layers may be omitted, or other functional layers may be added as needed.

[0315] The organic material layer containing the heterocyclic compound of formula 1 may contain other materials as needed.

[0316] In an organic light-emitting element according to one embodiment of this specification, materials other than heterocyclic compounds of Formula 1 are shown below. However, these are for illustrative purposes only and are not intended to limit the scope of this application, and these materials may be replaced by materials known in the art.

[0317] As anode materials, materials with relatively large work functions can be used, and transparent conductive oxides, metals, conductive polymers, or the like can be used. Specific examples of anode materials include: metals, such as vanadium, chromium, copper, zinc, and gold or their alloys; metal oxides, such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides, such as ZnO:Al or SnO2:Sb; conductive polymers, such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, and the like, but not limited thereto.

[0318] Materials with relatively small work functions can be used as cathode materials, and metals, metal oxides, conductive polymers, or the like can be used. Specific examples of cathode materials include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or their alloys; multilayer materials such as LiF / Al or LiO2 / Al and the like, but are not limited thereto.

[0319] As a hole injection material, known hole injection materials can be used, and for example, phthalocyanine compounds, such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429; or star-shaped catalytic amine derivatives, such as tris(4-carbazoyl-9-ylphenyl)amine (TCTA), 4,4',4”-tri[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA), and 1,3,5-tris[4-(3-methylphenylaniline)phenyl]benzene (1,3,5-tris[4-(3-methylphenylaniline)phenyl]benzene (m-MTDATA), as described in the literature [Advanced Material, 6, p. 677 (1994)]. Polyaniline / dodecylbenzenesulfonic acid, poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate), polyaniline / camphorsulfonic acid or polyaniline / poly(4-styrenesulfonate) and the like are conductive polymers with solubility.

[0320] As hole-transfer materials, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, and similar materials can be used, as well as low-molecular-weight or high-molecular-weight materials. For example, N,N'-di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (NPB) can be used.

[0321] Bathocuproine (BCP) can be used as a hole-blocking material; however, hole-blocking materials are not limited to this.

[0322] Metal complexes of oxadiazole derivatives, anthraquinone dimethyl ether and their derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinone dimethyl ether and its derivatives, fluorenone derivatives, diphenyl dicyanoethylene and its derivatives, dibenzoquinone derivatives, 8-hydroxyquinoline and its derivatives, and similar compounds can be used as electron transfer materials, as well as polymeric and low-molecular-weight materials. For example, tris(8-hydroxyquinoline)aluminum (Alq3) can be used.

[0323] LiF is commonly used as an example of an electron-injection material in this technology; however, this application is not limited to this.

[0324] Red, green, or blue luminescent materials can be used, and two or more luminescent materials can be mixed and used as needed. In this document, the two or more luminescent materials can be deposited individually from a single supply source or premixed and deposited using a single supply source. Additionally, fluorescent materials can also be used as luminescent materials; however, phosphorescent materials can also be used. As luminescent materials, materials that emit light by combining holes and electrons injected from the anode and cathode respectively can be used alone; however, materials having a host material and a dopant material that participate in luminescence together can also be used.

[0325] When mixing luminescent material substrates, substrates from the same series or different series can be mixed. For example, any two or more materials from N-type or P-type substrate materials can be selected and used as the substrate material for the luminescent layer.

[0326] An organic light-emitting element according to one embodiment of this specification may be a top-emission type, a bottom-emission type, or a dual-emission type, depending on the material used.

[0327] The compounds according to one embodiment of this specification can also be used in organic electronic components, including organic solar cells, organic photoconductors, organic transistors and the like, based on similar principles used in organic light-emitting elements.

[0328] Methods of implementing the present invention

[0329] The present specification will be described in more detail below with reference to examples; however, these are for illustrative purposes only, and the scope of this application is not limited thereto.

[0330] <Preparation Example 1> Preparation of Intermediate A

[0331]

[0332] 1) Preparation of intermediate A-3

[0333] 1,8-Dibromonaphthalene (20.0 g, 69.9 mmol / L), (4-chloro-2-methoxyphenyl)boronic acid (13.0 g, 69.9 mmol / L), Pd(PPh3)4(tetra(triphenylphosphine)palladium(0)) (4.0 g, 3.5 mmol / L) and K2CO3 (19.3 g, 140.0 mmol / L) were dissolved in 1,4-dioxane / water (1,4-dioxane / H2O) (200 mL / 40 mL) and refluxed for 12 hours. After the reaction was complete, the product was extracted by introducing distilled water and dichloromethane (DCM) at room temperature, and the solvent was removed using a rotary evaporator after drying the organic layer with MgSO4. The reaction material was purified by column chromatography (DCM:Hex = 1:6) to obtain intermediate A-3 (17.0 g, 70%).

[0334] Hex refers to hexane.

[0335] 2) Preparation of intermediate A-2

[0336] Intermediate A-3 (17.0 g, 48.9 mmol / L) and BBr3 (boron tribromide) (13.9 mL, 146.7 mmol / L) were dissolved in DCM (200 mL) and reacted at room temperature for 6 hours. After the reaction was complete, the product was extracted by introducing distilled water and DCM at room temperature, and the solvent was removed by rotary evaporation after drying the organic layer with MgSO4. The reaction material was purified by column chromatography (DCM:Hex = 1:1) and recrystallized from methanol to obtain intermediate A-2 (14.7 g, 90%).

[0337] 3) Preparation of intermediate A-1

[0338] Intermediate A-2 (14.7 g, 44.1 mmol / L) and Cs₂CO₃ (28.7 g, 88.2 mmol / L) were dissolved in N,N-dimethylacetamide (DMA) (150 mL) and refluxed for 12 hours. After the reaction was complete, the product was extracted by introducing distilled water and DCM at room temperature, and the solvent was removed by rotary evaporation after drying the organic layer with MgSO₄. The reaction material was purified by column chromatography (DCM:Hex = 1:1) and recrystallized from methanol to obtain intermediate A-1 (9.5 g, 85%).

[0339] 4) Preparation of intermediate A

[0340] Intermediate A-1 (9.5 g, 37.6 mmol / L) and n-bromosuccinimide (NBS) (7.4 g, 41.4 mmol / L) were dissolved in CHCl3 (chloroform) (100 mL) and refluxed for 24 hours. After the reaction was complete, the product was recrystallized from methanol to obtain intermediate A (10.1 g, 81%).

[0341] Apart from intermediate A in Preparation Example 1, compounds including benzo[kl]xanthones (e.g., intermediate A1 in Table 2 below) used to synthesize the compounds disclosed herein can be synthesized using techniques known in this art.

[0342] <Preparation Example 2> Preparation of Compound 1-1

[0343]

[0344] 1) Preparation of intermediate 1-1-1

[0345] Intermediate A (10.0 g, 30.2 mmol / L), phenylboronic acid (5.5 g, 45.3 mmol / L), Pd(PPh3)4 (1.7 g, 1.5 mmol / L), and K2CO3 (8.3 g, 60.4 mmol / L) from Preparation Example 1 were dissolved in 1,4-dioxane / water (100 mL / 20 mL) and refluxed for 6 hours. After the reaction was complete, the product was extracted by introducing distilled water and DCM at room temperature, and the solvent was removed by rotary evaporation after drying the organic layer with MgSO4. The reaction material was purified by column chromatography (DCM:Hex = 1:3) and recrystallized from methanol to obtain intermediate 1-1-1 (9.0 g, 91%).

[0346] 2) Preparation of compound 1-1

[0347] Intermediate 1-1-1 (9.0 g, 27.4 mmol / L), N-phenyl-[1,1'-biphenyl]-4-amine (6.7 g, 27.4 mmol / L), Pd2(dba)3 (tris(dibenzylacetone)dipalladium(0)) (1.3 g, 1.4 mmol / L), XPhos (2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl) (1.3 g, 2.7 mmol / L), and t-BuONa (sodium tert-butoxide) (3.9 g, 41.1 mmol / L) were dissolved in xylene (100 mL) and refluxed for 6 hours. After the reaction was complete, the product was extracted by introducing distilled water and DCM at room temperature, and the solvent was removed using a rotary evaporator after drying the organic layer with MgSO4. The reaction material was purified by column chromatography (DCM:Hex = 1:4) to obtain the target compound 1-1 (12.1 g, 82%).

[0348] Except for replacing phenylboronic acid with compound B from Table 1 and replacing N-phenyl-[1,1'-biphenyl]-4-amine with compound C from Table 1, the target compound A from Table 1 was synthesized in the same manner as in Preparation Example 2.

[0349] [Table 1]

[0350]

[0351]

[0352]

[0353]

[0354] Except that intermediate A was replaced by intermediate A in Table 2 and N-phenyl-[1,1'-biphenyl]-4-amine was replaced by compound C in Table 2, the target compound A in Table 2 was synthesized in the same manner as in Preparation Example 2.

[0355] [Table 2]

[0356]

[0357]

[0358] <Preparation Example 3> Preparation of Compounds 1-8

[0359]

[0360] 1) Preparation of intermediate 1-8-1

[0361] Intermediate A (10.0 g, 30.2 mmol / L), phenylboronic acid (5.5 g, 45.3 mmol / L), Pd(PPh3)4 (1.7 g, 1.5 mmol / L), and K2CO3 (8.3 g, 60.4 mmol / L) from Preparation Example 1 were dissolved in 1,4-dioxane / water (100 mL / 20 mL) and refluxed for 6 hours. After the reaction was complete, the product was extracted by introducing distilled water and DCM at room temperature, and the solvent was removed by rotary evaporation after drying the organic layer with MgSO4. The reaction material was purified by column chromatography (DCM:Hex = 1:3) and recrystallized from methanol to obtain intermediate 1-8-1 (9.0 g, 91%).

[0362] 2) Preparation of compounds 1-8

[0363] Intermediate 1-8-1 (9.0 g, 27.4 mmol / L), (4-(di([1,1'-biphenyl]-4-yl)amino)phenyl)boronic acid (12.1 g, 27.4 mmol / L), Pd2(dba)3 (1.3 g, 1.4 mmol / L), XPhos (1.3 g, 2.7 mmol / L), and K2CO3 (11.4 g, 82.2 mmol / L) were dissolved in 1,4-dioxane / water (100 mL / 20 mL) and refluxed for 6 hours. After the reaction was complete, the product was extracted with distilled water and DCM at room temperature, and the solvent was removed by rotary evaporator after drying the organic layer with MgSO4. The reaction material was purified by column chromatography (DCM:Hex = 1:3) to obtain target compound 1-8 (15.7 g, 83%).

[0364] Except for replacing (4-(bis([1,1'-biphenyl]-4-yl)amino)phenyl)boronic acid with compound C from Table 3 below, the target compound A in Table 3 below was synthesized in the same manner as in Preparation Example 3.

[0365] [Table 3]

[0366]

[0367]

[0368] <Preparation Example 4> Preparation of Compound 1-141

[0369]

[0370] 1) Preparation of intermediate 1-141-2

[0371] Intermediate A-1 (10.0 g, 39.6 mmol / L), phenylboronic acid (7.2 g, 59.4 mmol / L), Pd2(dba)3 (1.8 g, 2.0 mmol / L), XPhos (2.8 g, 5.9 mmol / L), and NaOH (3.2 g, 79.2 mmol / L) from Preparation Example 1 were dissolved in toluene / ethanol / water (toluene / EtOH / H2O) (100 mL / 20 mL / 20 mL) and refluxed for 6 hours. After the reaction was complete, the product was extracted by introducing distilled water and DCM at room temperature, and the solvent was removed by rotary evaporator after drying the organic layer with MgSO4. The reaction material was purified by column chromatography (DCM:Hex = 1:5) and recrystallized from methanol to obtain intermediate 1-141-2 (8.2 g, 70%).

[0372] 2) Preparation of intermediate 1-141-1

[0373] Intermediate 1-141-2 (8.2 g, 27.9 mmol / L) and NBS (5.5 g, 30.7 mmol / L) were dissolved in CHCl3 (100 mL) and refluxed for 24 hours. After the reaction was complete, the product was recrystallized from methanol to obtain intermediate 1-141-1 (8.2 g, 79%).

[0374] 3) Preparation of compound 1-141

[0375] Intermediate 1-141-1 (8.2 g, 22.0 mmol / L), di([1,1'-biphenyl]-4-yl)amine (7.1 g, 22.0 mmol / L), Pd2(dba)3 (1.0 g, 1.4 mmol / L), t-Bu3P (tristerylphosphine) (1.0 mL, 2.2 mmol / L), and t-BuONa (4.2 g, 44.0 mmol / L) were dissolved in toluene (100 mL) and refluxed for 12 hours. After the reaction was complete, the product was extracted with distilled water and DCM at room temperature, and the solvent was removed by rotary evaporator after drying the organic layer with MgSO4. The reaction material was purified by column chromatography (DCM:Hex = 1:7) to obtain the target compound 1-141 (11.2 g, 83%).

[0376] Except for replacing phenylboronic acid with compound B from Table 4 and replacing di([1,1'-biphenyl]-4-yl)amine with compound C from Table 4, the target compound A from Table 4 was synthesized in the same manner as in Preparation Example 4.

[0377] [Table 4]

[0378]

[0379]

[0380]

[0381]

[0382] <Preparation Example 5> Preparation of Compound 1-148

[0383]

[0384] 1) Preparation of intermediate 1-148-2

[0385] Intermediate A-1 (10.0 g, 39.6 mmol / L), phenylboronic acid (7.2 g, 59.4 mmol / L), Pd2(dba)3 (1.8 g, 2.0 mmol / L), XPhos (2.8 g, 5.9 mmol / L), and NaOH (3.2 g, 79.2 mmol / L) from Preparation Example 1 were dissolved in toluene / ethanol / water (toluene / EtOH / H2O) (100 mL / 20 mL / 20 mL) and refluxed for 6 hours. After the reaction was complete, the product was extracted by introducing distilled water and DCM at room temperature, and the solvent was removed by rotary evaporator after drying the organic layer with MgSO4. The reaction material was purified by column chromatography (DCM:Hex = 1:5) and recrystallized from methanol to obtain intermediate 1-148-2 (8.2 g, 70%).

[0386] 2) Preparation of intermediate 1-148-1

[0387] Intermediate 1-148-2 (8.2 g, 27.9 mmol / L) and NBS (5.5 g, 30.7 mmol / L) were dissolved in CHCl3 (100 mL) and refluxed for 24 hours. After the reaction was complete, the product was recrystallized from methanol to obtain intermediate 1-148-1 (8.2 g, 79%).

[0388] 3) Preparation of compound 1-148

[0389] Intermediate 1-148-1 (8.2 g, 22.0 mmol / L), (4-(di([1,1'-biphenyl]-4-yl)amino)phenyl)boronic acid (9.7 g, 22.0 mmol / L), Pd(PPh3)4 (1.3 g, 1.1 mmol / L), and K2CO3 (6.1 g, 44.0 mmol / L) were dissolved in 1,4-dioxane / water (1,4-dioxane / H2O) (100 mL / 20 mL) and refluxed for 24 hours. After the reaction was complete, the product was extracted with distilled water and DCM at room temperature, and the solvent was removed by rotary evaporator after drying the organic layer with MgSO4. The reaction material was purified by column chromatography (DCM:Hex = 1:4) to obtain the target compound 1-148 (13.5 g, 89%).

[0390] Except for replacing (4-(bis([1,1'-biphenyl]-4-yl)amino)phenyl)boronic acid with compound C from Table 5 below, target compound A from Table 5 below was synthesized in the same manner as in Preparation Example 5.

[0391] [Table 5]

[0392]

[0393] The compounds other than those described in Tables 1 to 5 were also prepared using the same methods as those described in the preparation examples above. The synthetic identification results of the compounds prepared above are shown in Tables 6 and 7 below. Table 6 shows... 1 The measurements were obtained by nuclear magnetic resonance (NMR) (CDCl3, 200 MHz), and Table 7 shows the measurements obtained by field desorption (FD)-mass spectrometry (FD-MS).

[0394] [Table 6]

[0395]

[0396]

[0397]

[0398] [Table 7]

[0399]

[0400] <Experimental Example 1>

[0401] 1) Manufacturing of organic light-emitting elements

[0402] Comparative Example 1

[0403] The glass substrate on which an ITO film with a thickness of 1,500 angstroms was coated was cleaned using distilled water ultrasonic cleaning. After cleaning with distilled water, the substrate was ultrasonically cleaned with solvents such as acetone, methanol, and isopropanol, then dried, and treated with ultraviolet ozone (UVO) for 5 minutes using an ultraviolet (UV) cleaner. Following this, the substrate was transferred to a plasma cleaner (PT) and subjected to plasma treatment under vacuum to achieve the ITO work function and remove residual film. The substrate was then transferred to an apparatus for organic deposition.

[0404] The following 4,4',4”-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) is introduced into a cell of a vacuum deposition apparatus.

[0405]

[0406] Then, the chamber was evacuated until the vacuum level reached 10. -6 To deposit a hole injection layer with a thickness of 600 angstroms on an ITO substrate, 2-TNATA is evaporated by applying current to the cells.

[0407] The following N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) is introduced into another cell in the vacuum deposition apparatus, and NPB is evaporated by applying an electric current to the cell to deposit a hole transfer layer with a thickness of 300 angstroms on the hole injection layer.

[0408]

[0409] The following is a thermal vacuum deposition of the light-emitting layer on the hole transfer layer. As the light-emitting layer, a compound of 9-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-9'-phenyl-3,3'-bis-9H-carbazole was deposited to a thickness of 400 Å as the host, and Ir(ppy)3 was doped and deposited at a concentration of 7% as a green phosphorescent dopant. Following this, BCP was deposited to a thickness of 60 Å as a hole-blocking layer, and Alq3 was deposited on top of it to a thickness of 200 Å as an electron transfer layer. Finally, an electron injection layer was formed on the electron transfer layer by depositing lithium fluoride (LiF) to a thickness of 10 Å, and then a cathode was formed on the electron injection layer by depositing an aluminum (Al) cathode to a thickness of 1,200 Å. Thus, the organic light-emitting element of Comparative Example 1 was fabricated.

[0410] At the same time, for each material to be used in the manufacture of organic light-emitting elements, in 10 -8 Up to 10 -6 All the organic compounds required for manufacturing organic light-emitting elements were purified by vacuum sublimation.

[0411] Examples 1 to 60

[0412] The organic light-emitting elements of Examples 1 to 60 were manufactured in the same manner as those used to manufacture the organic light-emitting element of Comparative Example 1, except that the compounds of Examples 1 to 60 in Table 8 below were used instead of the compound NPB used to form the hole transfer layer in Comparative Example 1.

[0413] Comparative Examples 2 to 7

[0414] Except that each of the compounds M1 to M6 in Table 8 below was used instead of the compound NPB used in forming the hole transfer layer in Comparative Example 1, the organic light-emitting elements of Comparative Examples 2 to 7 were manufactured in the same manner as those used to manufacture the organic light-emitting element of Comparative Example 1.

[0415] In this article, the compounds M1 to M6 used in Comparative Examples 2 to 7 are as follows.

[0416]

[0417] (2) Driving voltage and luminous efficiency of organic light-emitting elements

[0418] For each organic light-emitting element of Examples 1 to 60 and Comparative Examples 1 to 7 manufactured as described above, the electroluminescence (EL) properties were measured using an M7000 manufactured by McScience Inc., and based on the measurement results, the lifetime of the element at a standard luminance of 6,000 candela / m² (cd / m²) was measured using a lifetime measurement system (M6000) manufactured by McScience Inc. 2 The lifespan T at that time90 (Unit: h, hours), which is the time it takes for the initial brightness to become 90%.

[0419] The properties of the organic light-emitting element disclosed herein, as shown in the measurement results, are illustrated in Table 8 below.

[0420] [Table 8]

[0421]

[0422]

[0423]

[0424] As described in Table 8, the organic light-emitting elements of Examples 1 to 60, which use heterocyclic compounds of Formula 1 according to the present disclosure to form hole transfer layers, have the properties of long lifetime, low voltage and high efficiency.

[0425] Specifically, the organic light-emitting elements of Examples 1 to 60 have a structure in which benzo[kl]xanthine is substituted with two substituents (i.e., amino and aryl), which delocalizes the HOMO (highest occupied molecular orbital) energy level, thereby increasing hole transfer capability and stabilizing the HOMO energy. Accordingly, when a heterocyclic compound of Formula 1 is used as the material of the hole transfer layer in the organic light-emitting element, an appropriate energy level and band gap are formed, thereby increasing the excitons in the luminescent region. Increasing the excitons in the luminescent region means having the effect of reducing the driving voltage of the element and increasing efficiency. It was identified that, compared with the organic light-emitting elements of Examples 1 to 60, when the hole transfer layer is formed, the organic light-emitting elements of Comparative Examples 1 to 7 without using the compound according to this application have reduced luminous efficiency and lifetime.

[0426] Specifically, it was identified that the use of deuterium-substituted compounds in Examples 6 and 29 was effective in further improving the driving voltage, luminous efficiency, and lifetime. Specifically, compounds 1-145 of Example 27 and compounds 1-149 of Example 29 have the same structure but different deuterium substitution, and it was observed that the deuterium-substituted Examples 29 exhibited superior driving voltage, luminous efficiency, and lifetime compared to Example 27.

[0427] <Experimental Example 2>

[0428] (1) Manufacturing of organic light-emitting elements

[0429] Comparative Example 8

[0430] The transparent ITO electrode film obtained from the glass used in the organic light-emitting element (manufactured by Samsung-Corning Co., Ltd.) was continuously ultrasonically cleaned for 5 minutes each using trichloroethylene, acetone, ethanol, and distilled water, and then stored in isopropanol for use. Next, the ITO substrate was mounted in the substrate holder of the vacuum deposition apparatus, and 4,4',4”-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) was introduced into the cell of the vacuum deposition apparatus.

[0431]

[0432] Then, the chamber was evacuated until the vacuum level reached 10. -6 To deposit a hole injection layer with a thickness of 600 angstroms on an ITO substrate, 2-TNATA is evaporated by applying current to the cell. N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) is introduced into another cell of the vacuum deposition apparatus, and NPB is evaporated by applying current to the cell to deposit a hole transfer layer with a thickness of 300 angstroms on the hole injection layer.

[0433]

[0434] After forming the hole injection layer and hole transfer layer as described above, M7 is deposited to a thickness of 50 angstroms as an electron blocking layer, and a blue luminescent material with the following structure is deposited on it as a luminescent layer. Specifically, in a side cell of a vacuum deposition apparatus, the blue luminescent host material H1 is vacuum deposited to a thickness of 200 angstroms, and a blue luminescent dopant material D1 is vacuum deposited on it at an amount of 5% relative to the host material.

[0435]

[0436] Subsequently, a compound with the following structural formula E1 was deposited to a thickness of 300 angstroms as an electron transfer layer.

[0437]

[0438] Lithium fluoride (LiF) was deposited to a thickness of 10 angstroms as the electron injection layer, and an Al cathode was used to a thickness of 1,000 angstroms, thus fabricating an organic light-emitting element. Meanwhile, for each material to be used in the fabrication of the organic light-emitting element, a thickness of 10 angstroms was determined. -8 Up to 10 -6 All the organic compounds required for manufacturing organic light-emitting elements were purified by vacuum sublimation.

[0439] Comparative Examples 9 and 10 and Examples 61 to 120

[0440] The organic light-emitting element was manufactured in the same manner as the organic light-emitting element used in Comparative Example 8, except that the electron blocking layer was formed by replacing M7 with the compounds in Table 9 below.

[0441] In this paper, the electron blocking layer compounds M7 to M9 of Comparative Examples 8 to 10 are as follows.

[0442]

[0443] (2) Driving voltage and luminous efficiency of organic light-emitting elements

[0444] For each organic light-emitting element manufactured as described above in Examples 61 to 120 and Comparative Examples 8 to 10, the electroluminescence (EL) properties were measured using an M7000 manufactured by Macquarie Scientific, and based on the measurement results, the lifetime T at a standard luminance of 6,000 candela / m² was measured using a lifetime measurement system (M6000) manufactured by Macquarie Scientific. 95 (Unit: h, hours), which is the time it takes for the initial brightness to become 95%.

[0445] The properties of the organic light-emitting element disclosed herein, as shown in the measurement results, are illustrated in Table 9 below.

[0446] [Table 9]

[0447]

[0448]

[0449] According to Experimental Example 2, it was identified that, compared with the organic light-emitting elements of Comparative Examples 8 to 10 that did not use the compound according to this application when forming the electron blocking layer, the organic light-emitting elements of Examples 61 to 120 that used the compound according to this application when forming the electron blocking layer have excellent electron blocking ability by delocalizing the HOMO (highest occupied molecular orbital) energy level and stabilizing the HOMO energy, and have excellent luminous efficiency and lifetime.

Claims

1. A heterocyclic compound of the following chemical formula 1: [Chemical Formula 1] in, In chemical formula 1, One of R1 to R10 is -(L)lN(R24)(R25); The other one of R1 to R10 is an unsubstituted or deuterated C6 to C20 aryl group; the remaining ones of R1 to R10 are each independently hydrogen; or deuterium; L is a direct bond; or an unsubstituted or deuterated C6 to C15 arylene group; l is 1; and R24 and R25 may be the same as or different from each other, and each independently is an unsubstituted or deuterated phenyl; an unsubstituted or deuterated biphenyl; an unsubstituted or deuterated terphenyl; an unsubstituted or deuterated naphthyl; an unsubstituted or deuterated phenanthryl; an unsubstituted or deuterated fluorenyl or substituted with one or more substituents selected from deuterium, methyl and phenyl, and not spirofluorenyl; an unsubstituted or deuterated dibenzofuranyl or substituted with one or more substituents selected from deuterium and phenyl; or an unsubstituted or deuterated dibenzothiophenyl or substituted with one or more substituents selected from deuterium and phenyl.

2. The heterocyclic compound according to claim 1, wherein chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-4: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formulas 1-3] [Chemical Formulas 1-4] In chemical formulas 1-1 to 1-4, L, l, R24, and R25 have the same definitions as in Formula 1; Ar is an unsubstituted or deuterated C6 to C20 aryl group; R41 and R42 are each independently hydrogen; or deuterium; r41 is an integer from 0 to 3, r42 is an integer from 0 to 5, r43 is an integer from 0 to 2, r44 is an integer from 0 to 6, and r45 and r46 are each integers from 0 to 4; and When r41, r42, and r44 to r46 are 2 or greater than 2, or when r43 is 2, the substituents in parentheses are the same or different from each other.

3. The heterocyclic compound according to claim 1, wherein -(L)lN(R24)(R25) is represented by any one of the following chemical formulas N-1 to N-3: [Chemical formula N-1] [Chemical formula N-2] [Chemical formula N-3] In chemical formulas N-1 to N-3, L and l have the same definitions as in chemical formula 1; X and Y are each independently O; or S; Ar1 and Ar2 may be the same as or different from each other, and each is independently an unsubstituted or deuterated phenyl; an unsubstituted or deuterated biphenyl; an unsubstituted or deuterated terphenyl; an unsubstituted or deuterated naphthyl; an unsubstituted or deuterated phenanthryl; an unsubstituted or deuterated fluorenyl or fluorenyl selected from deuterium, methyl and phenyl with one or more substituents, and not spirofluorenyl; R31 and R32 are each independently hydrogen; deuterium; or phenyl; and r31 and r32 are each integers from 0 to 7, and when r31 and r32 are each 2 or greater than 2, the substituents in parentheses are the same or different from each other.

4. The heterocyclic compound according to claim 1, wherein chemical formula 1 has a deuterium content of 0% or from 10% to 100%.

5. The heterocyclic compound according to claim 1, wherein chemical formula 1 is represented by any of the following compounds: 。 6. An organic light-emitting element, comprising: First electrode; Second electrode; as well as One or more organic material layers are disposed between the first electrode and the second electrode. One or more of the organic material layers contain a heterocyclic compound as described in any one of claims 1 to 5.

7. The organic light-emitting element according to claim 6, wherein the organic material layer comprises a hole transfer layer, and the hole transfer layer contains the heterocyclic compound.

8. The organic light-emitting element according to claim 6, wherein the organic material layer comprises an electron blocking layer, and the electron blocking layer contains the heterocyclic compound.

9. The organic light-emitting element according to claim 6 further comprises one, two, or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transfer layer, an electron injection layer, an electron transfer layer, an electron blocking layer, and a hole blocking layer.

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