Compound and organic light emitting element including the same

Abstract

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

Description

[0001] This specification claims priority and benefits to Korean Patent Application No. 10-2020-0155675, filed on November 19, 2020, with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field

[0002] This specification relates to a compound and an organic light-emitting element comprising the same. Background Technology

[0003] Electroluminescent elements are self-emissive display elements with advantages such as wide viewing angle, high response speed, and excellent contrast.

[0004] 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, and emit light as they annihilate. The organic thin film can be formed as a single layer or multiple layers as needed.

[0005] 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 of a light-emitting layer based on a host dopant can be used. In addition, compounds capable of functioning as hole injection, hole transport, electron blocking, and electron transport can also be used as materials for organic thin films.

[0006] To improve the performance, lifespan, or efficiency of organic light-emitting elements, there has always been a need to develop organic thin film materials. Summary of the Invention

[0007] Technical issues

[0008] This specification relates to providing a compound and an organic light-emitting element including the same.

[0009] Technical solutions

[0010] One embodiment of this specification provides a compound having the following chemical formula 1.

[0011] [Chemical Formula 1]

[0012]

[0013] In chemical formula 1,

[0014] X is O; S; or CR'R".

[0015] R' and R” are each independently a substituted or unsubstituted C1 to C60 alkyl; a substituted or unsubstituted C6 to C60 aryl; or a substituted or unsubstituted C2 to C60 heteroaryl.

[0016] L1, L2, L11, and L12 are each independently a direct bond; substituted or unsubstituted C6 to C60 arylene groups; or substituted or unsubstituted C2 to C60 heteroarylene groups.

[0017] R11, R12, and Ar are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0018] R1 is hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or unsubstituted C6 to C60 aryl group; or substituted or unsubstituted C2 to C60 heteroaryl group.

[0019] r is an integer from 0 to 8, and when r is 2 or greater than 2, R1 is either the same or different from each other.

[0020] The term "substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of: deuterium; halogen; cyano; C1 to C60 alkyl; C2 to C60 alkenyl; C2 to C60 alkynyl; C3 to C60 cycloalkyl; C2 to C60 heterocycloalkyl; C6 to C60 aryl; and C2 to C60 heteroaryl, or substituted with a substituent connected to two or more substituents selected from the above substituents, or unsubstituted.

[0021] Another embodiment of this specification provides an organic light-emitting element, the organic light-emitting element comprising: a first electrode; a second electrode disposed opposite to the first electrode; and an organic material layer disposed between the first electrode and the second electrode, wherein the organic material layer comprises the compound of chemical formula 1.

[0022] Beneficial effects

[0023] The compounds described in this specification can be used as materials for the organic material layer of organic light-emitting elements. These compounds can function as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, charge generation materials, etc. Specifically, these compounds can be used as materials for the hole transport layer or electron blocking layer of organic light-emitting elements.

[0024] When compounds of Formula 1 are used as materials for the hole transport layer or electron blocking layer of organic light-emitting elements, organic light-emitting elements with excellent properties in terms of driving voltage and lifetime can be provided.

[0025] Specifically, by bonding substituents with enhanced hole-carrying properties to the amine-substituted fluorene framework of a compound of Formula 1, when used as a hole transport layer, the non-shared electron pairs of the amine improve hole flow, thereby enhancing the hole transport capability of the hole transport layer by adjusting the band gap and T1 (energy level value in the triplet state). Furthermore, when used as an electron blocking layer, it can suppress the degradation of the hole transport material caused by electron intrusion into the hole transport layer, thus providing an organic light-emitting element with excellent efficiency. In addition, the increased planarity and glass transition temperature of the compound improve its thermal stability. Attached Figure Description

[0026] Figures 1 to 4 These are diagrams illustrating the stacked structure of an organic light-emitting element according to one embodiment of this specification.

[0027] Explanation of icon numbers

[0028] 100:Substrate

[0029] 200: Anode

[0030] 300: Organic material layer

[0031] 301: Hole Injection Layer

[0032] 302: Hole transport layer

[0033] 303: Electron blocking layer

[0034] 304: Emissive layer

[0035] 305: Electron Transport Layer

[0036] 306: Electron Injection Layer

[0037] 400: Cathode Detailed Implementation

[0038] This instruction manual will be described in more detail below.

[0039] In this specification, the description of a particular part "including" a particular component means that it may further include other components, and does not exclude other components, unless specifically stated to the contrary.

[0040] The term "substitution" refers to the replacement of a hydrogen atom bonded to a carbon atom of a compound with 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 substitute), and when two or more substituents are substituted, the two or more substituents may be the same as or different from each other.

[0041] In this specification, "substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of: deuterium; halogen; cyano; C1 to C60 alkyl; C2 to C60 alkenyl; C2 to C60 alkynyl; C3 to C60 cycloalkyl; C2 to C60 heterocycloalkyl; C6 to C60 aryl; and C2 to C60 heteroaryl, or substituted with a substituent connected to two or more substituents selected from the above substituents, or unsubstituted.

[0042] In this specification, "in the absence of a substituent in the chemical formula or compound structure" refers to a bond between a hydrogen atom and a carbon atom. However, since deuterium (2H) is an isotope of hydrogen, some hydrogen atoms can be deuterium.

[0043] In one embodiment of this application, "where no substituent is specified in the chemical formula or compound structure" may mean that all positions that can serve as substituents may 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 0% to 100%.

[0044] In one embodiment of this application, when "no substituents are specified in the chemical formula or compound structure", hydrogen and deuterium can 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).

[0045] In one embodiment of this application, deuterium is an isotope of hydrogen, an element having a deuterium nucleus formed by a proton and a neutron, and can be represented as hydrogen-2, and its element symbol can also be written as D or 2H.

[0046] In one embodiment of this application, an isotope refers to an atom having the same atomic number (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.

[0047] 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 particular substituent is defined as T2, the meaning of the content T% of the particular substituent can be defined as T2 / T1×100=T.

[0048] In other words, in one instance, in the case of... The 20% deuterium content in a phenyl group indicates 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 20% deuterium content in a phenyl group can be represented by the following structural formula.

[0049]

[0050] Furthermore, in one embodiment of this application, "the deuterium content of the phenyl is 0%" may refer to a phenyl that does not contain deuterium atoms, that is, a phenyl with 5 hydrogen atoms.

[0051] In this specification, halogen may be fluorine, chlorine, bromine or iodine.

[0052] 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 from 1 to 60, specifically from 1 to 40, and more specifically from 1 to 20. Specific examples may include 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, etc., but are not limited to these.

[0053] 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 2 to 60, specifically 2 to 40, and more specifically 2 to 20. Specific examples may include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbene, styrene, etc., but are not limited thereto.

[0054] 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 may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20.

[0055] In this specification, cycloalkyl includes monocyclic or polycyclic cycloalkyl groups having 3 to 60 carbon atoms, and may be further substituted with other substituents. Polycyclic refers to a group in which the cycloalkyl group is directly attached to or fused with other cyclic groups. Other cyclic groups may be cycloalkyl, but may also be different types of cyclic groups, such as heterocycloalkyl, aryl, and heteroaryl. The number of carbon groups in a cycloalkyl group may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specific examples may include 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, etc., but are not limited thereto.

[0056] In this specification, heterocyclic alkyl groups include O, S, Se, N, or Si as heteroatoms, and include monocyclic or polycyclic heterocyclic alkyl groups having 2 to 60 carbon atoms, and may be further substituted with other substituents. Polycyclic refers to a group in which the heterocyclic alkyl group is directly attached 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 2 to 60, specifically 2 to 40, and more specifically 3 to 20.

[0057] In this specification, aryl groups include monocyclic or polycyclic aryl groups having 6 to 60 carbon atoms, and may be further substituted with other substituents. Polycyclic refers to a group in which the aryl group is directly attached 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 6 to 60, specifically 6 to 40, and more specifically 6 to 25. When the aryl group is bicyclic or higher, the number of carbon atoms may be 8 to 60, 8 to 40, or 8 to 30. Specific examples of aryl groups may include phenyl, biphenyl, terphenyl, naphthyl, anthracene, etc. The group includes, but is not limited to, phenanthrene, perylene, fluoranthracene, dithionylene, fenylene, pyrene, fused tetraphenyl, fused pentaphenyl, fluorenyl, indene, acenaphthene, benzofluorenyl, spirodifluorenyl, 2,3-dihydro-1H-indene, and its fused cyclic groups.

[0058] In this specification, terphenyl may be selected from the following structures.

[0059]

[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, it may include However, the structure is not limited to this.

[0062] In this specification, heteroaryl groups include O, S, SO2, Se, N, or Si as heteroatoms, and include monocyclic or polycyclic heteroaryl groups, which may be further substituted with other substituents. Polycyclic here means a group in which the heteroaryl group is directly attached to or fused with other cyclic groups. Other cyclic groups here may be heteroaryl groups, but may also be different types of cyclic groups, such as cycloalkyl, heterocycloalkyl, and aryl groups. The number of carbon atoms in a heteroaryl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 25. When the heteroaryl group is bicyclic or higher, the number of carbon atoms may be 4 to 60, 4 to 40, or 4 to 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, dioxinyl group, triazinyl, tetrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, isoquinazolinyl, quinazolinyl, quinazolinyl (group), naphthidyl, acridineyl, phenanthridineyl, imidazopyridyl, diazanaphthyl, triazaindyl, indoleyl, benzothiazolyl, benzoxazolyl, benzoimidazolyl, benzothiophene, benzofuranyl, dibenzothiophene, dibenzofuranyl, carbazoleyl, benzocarbazoleyl, dibenzocarbazoleyl, phenazinyl, dibenzosilyl group), spirocyclic di(dibenzosilicyclopentadienyl), dihydrophenazinyl, phenoxazinyl, phenanthreneyl, indole[2,3-a]carbazoleyl, indole[2,3-b]carbazoleyl, indolinyl, 10,11-dihydro-dibenzo[b,f]-nitroheptenyl, 9,10-dihydroacridinyl, phenazinyl, phenthiazinyl, phthalazinyl, naphridinyl, phenolinyl Benz[c][1,2,5]thiadiazolyl, 5,10-dihydrobenzo[b,e][1,4]azasilinyl, pyrazolo[1,5-c]quinazolinyl, pyrido[1,2-b]inzolyl, pyrido[1,2-a]imidazo[1,2-e]dihydroindoleyl, 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]carbazole, benzofurano[2,3-b]carbazole, benzothieno[2,3-b]carbazole, 1,3-dihydroindolo[2,3-b]carbazole, benzofurano[3,2-b]carbazole, benzothieno[3,2-b]carbazole, 1,3-dihydroindolo[3,2-b]carbazole, benzofurano[2,3-c] Carbazolyl, benzothieno[2,3-c]carbazolyl, 1,3-dihydroindolo[2,3-c]carbazolyl, benzofurano[3,2-c]carbazolyl, benzothieno[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, etc., but not limited to these.

[0063] In this specification, except that the aryl group is a divalent group, the above examples of aryl groups can be applied to aryl groups.

[0064] In this specification, except that the heteroaryl group is a divalent group, the above examples of heteroaryl groups can be applied to heteroaryl groups.

[0065] In one embodiment of this specification, X may be 0.

[0066] In one embodiment of this specification, X may be S.

[0067] In one embodiment of this specification, X is CR'R", and R' and R" may each be independently a substituted or unsubstituted C1 to C60 alkyl; or a substituted or unsubstituted C6 to C60 aryl.

[0068] In one embodiment of this specification, X is CR'R", and R' and R" may each be independently C1 to C60 alkyl; or C6 to C60 aryl.

[0069] In one embodiment of this specification, X is CR'R", and R' and R" can each be independently C1 to C30 alkyl; or C6 to C30 aryl.

[0070] In one embodiment of this specification, X is CR'R", and R' and R" may each be independently C1 to C10 alkyl; or C6 to C10 aryl.

[0071] In one embodiment of this specification, X is CR'R", and R' and R" can each be independently C1 to C5 alkyl; or C6 to C10 aryl.

[0072] In one embodiment of this specification, X is CR'R", and R' and R" can each be independently methyl; or phenyl.

[0073] In one embodiment of this specification, chemical formula 1 may be represented by any of the following chemical formulas 1-1 to 1-3.

[0074] [Chemical Formula 1-1]

[0075]

[0076] [Chemical Formula 1-2]

[0077]

[0078] [Chemical Formulas 1-3]

[0079]

[0080] In chemical formulas 1-1 to 1-3,

[0081] R21 and R22 are each independently a substituted or unsubstituted C1 to C10 alkyl group; or a substituted or unsubstituted C6 to C20 aryl group, and

[0082] The remaining substituents have the same definitions as in Formula 1.

[0083] In one embodiment of this specification, R21 and R22 of chemical formulas 1-3 are each independently a substituted or unsubstituted C1 to C5 alkyl group; or a substituted or unsubstituted C6 to C10 aryl group.

[0084] In one embodiment of this specification, R21 and R22 are each independently C1 to C5 alkyl; or C6 to C10 aryl.

[0085] In one embodiment of this specification, R21 and R22 are each independently methyl; or phenyl.

[0086] In the embodiments described in this specification, L1 and L2 may each be a direct bond; or a C6 to C60 arylene group.

[0087] In the embodiments described in this specification, both L1 and L2 can be direct keys.

[0088] In the embodiments described in this specification, L1 is a C6 to C60 arylene, and L2 may be a direct bond.

[0089] In the embodiments described in this specification, L1 is a C6 to C30 arylene, and L2 may be a direct bond.

[0090] In the embodiments described in this specification, L1 is a phenylene oxide, and L2 may be a direct bond.

[0091] In the embodiments described in this specification, L1 is a direct bond, and L2 can be a C6 to C30 arylene.

[0092] In the embodiments described in this specification, L1 is a direct bond, and L2 may be a phenylene oxide.

[0093] In the embodiments described in this specification, L11 and L12 may each be a direct bond; or a C6 to C60 arylene group.

[0094] In one embodiment of this specification, both L11 and L12 can be direct keys.

[0095] In the embodiments described in this specification, L11 is a C6 to C60 arylene, and L12 may be a direct bond.

[0096] In the embodiments described in this specification, L11 is a C6 to C30 arylene, and L12 may be a direct bond.

[0097] In the embodiments described in this specification, L11 is a phenylene oxide, and L12 may be a direct bond.

[0098] In one embodiment of this specification, L11 and L12 may each be independently C6 to C60 arylene.

[0099] In one embodiment of this specification, L11 and L12 may each be independently C6 to C30 arylene.

[0100] In one embodiment of this specification, L11 and L12 may each be independently C6 to C10 arylene.

[0101] In one embodiment of this specification, both L11 and L12 may be phenylene.

[0102] In one embodiment of this specification, R11 and R12 are each independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0103] In one embodiment of this specification, R11 and R12 are each independently a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0104] In one embodiment of this specification, R11 and R12 are each independently a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0105] In one embodiment of this specification, R11 and R12 are each 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 fluorenyl; a substituted or unsubstituted dibenzofuranyl; or a substituted or unsubstituted dibenzothiopheneyl.

[0106] In one embodiment of this specification, R11 and R12 are each independently phenyl; biphenyl; terphenyl; naphthyl; unsubstituted or alkyl- or aryl-substituted fluorenyl; 9,9'-spirodi[fluorenyl]; dibenzofuranyl; or dibenzothiophene.

[0107] In one embodiment of this specification, R11 is a substituted or unsubstituted C6 to C60 aryl group, and R12 may be a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group containing O or S.

[0108] In one embodiment of this specification, R11 is a substituted or unsubstituted C6 to C30 aryl group, and R12 may be a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group containing O or S.

[0109] In one embodiment of this specification, R11 is an unsubstituted or alkyl- or aryl-substituted C6 to C30 aryl group, and R12 may be an unsubstituted or alkyl- or aryl-substituted C6 to C30 aryl group; or a C2 to C20 heteroaryl group containing O or S.

[0110] In one embodiment of this specification, R11 is a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted terphenyl; a substituted or unsubstituted naphthyl; or a substituted or unsubstituted fluorenyl.

[0111] In one embodiment of this specification, R11 is phenyl; biphenyl; terphenyl; naphthyl; unsubstituted or alkyl- or aryl-substituted fluorenyl; or 9,9'-spirodi[fluorene].

[0112] In one embodiment of this specification, R12 is a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted terphenyl; a substituted or unsubstituted naphthyl; a substituted or unsubstituted fluorenyl; a substituted or unsubstituted dibenzofuranyl; or a substituted or unsubstituted dibenzothiopheneyl.

[0113] In one embodiment of this specification, R12 is phenyl; biphenyl; terphenyl; naphthyl; unsubstituted or alkyl- or aryl-substituted fluorenyl; 9,9'-spirodi[fluorenyl]; dibenzofuranyl; or dibenzothiophene.

[0114] In one embodiment of this specification, Ar is a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0115] In one embodiment of this specification, Ar is a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0116] In one embodiment of this specification, Ar is a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0117] In one embodiment of this specification, Ar is a C6 to C20 aryl; or a C2 to C20 heteroaryl.

[0118] In one embodiment of this specification, Ar is a C6 to C20 aryl group; or a C2 to C20 heteroaryl group containing O or S.

[0119] In one embodiment of this specification, Ar is phenyl; biphenyl; terphenyl; naphthyl; ditriphenylene; dibenzofuranyl; or dibenzothiophene.

[0120] In one embodiment of this specification, Ar is not substituted with an amino group. Examples of amino groups here may include -NH2; monoalkylamino; monoarylamino; monoheteroarylamino; dialkylamino; diarylamino; diheteroarylamino; alkylarylamino; alkylheteroarylamino; arylheteroarylamino, etc.

[0121] In one embodiment of this specification, R1 is hydrogen; deuterium; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl.

[0122] In one embodiment of this specification, R1 is hydrogen; or deuterium.

[0123] In one embodiment of this specification, chemical formula 1 may be represented by the following chemical formula 2.

[0124] [Chemical Formula 2]

[0125]

[0126] In chemical formula 2,

[0127] Each substituent has the same definition as in Formula 1.

[0128] In one embodiment of this specification, chemical formula 1 may be represented by any of the following compounds, but is not limited thereto.

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146] 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 transport layer materials, light-emitting layer materials, electron transport 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.

[0147] Furthermore, by introducing various substituents into the structure of Formula 1, the 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.

[0148] 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 organic material layers comprise the compound of chemical formula 1.

[0149] In one embodiment of this specification, the first electrode may be an anode and the second electrode may be a cathode.

[0150] In another embodiment of this specification, the first electrode may be a cathode, and the second electrode may be an anode.

[0151] In one embodiment of this specification, the organic light-emitting element may be a blue organic light-emitting element, and the compound of Formula 1 may be used as a material for the blue organic light-emitting element. For example, the compound of Formula 1 may be contained in the hole transport layer or electron blocking layer of the blue organic light-emitting element.

[0152] In one embodiment of this specification, the organic light-emitting element may be a green organic light-emitting element, and the compound of Formula 1 may be used as a material for the green organic light-emitting element. For example, the compound of Formula 1 may be contained in the hole transport layer or electron blocking layer of the green organic light-emitting element.

[0153] In one embodiment of this specification, the organic light-emitting element may be a red organic light-emitting element, and the compound of Formula 1 may be used as a material for the red organic light-emitting element. For example, the compound of Formula 1 may be contained in the hole transport layer or electron blocking layer of the red organic light-emitting element.

[0154] In addition to using the above-mentioned compounds to form one or more organic material layers, the organic light-emitting elements in this specification can be manufactured using common organic light-emitting element manufacturing methods and materials.

[0155] When manufacturing organic light-emitting elements, solution coating and vacuum deposition methods can be used to form organic material layers from compounds. In this article, solution coating methods refer to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but are not limited to these.

[0156] The organic material layer of the organic light-emitting element 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 transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc., 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.

[0157] In the organic light-emitting element of this specification, the organic material layer includes a hole transport layer, and the hole transport layer may contain a compound of chemical formula 1.

[0158] 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 compound of chemical formula 1.

[0159] 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 transport layer, an electron injection layer, an electron transport layer, an electron blocking layer and a hole blocking layer.

[0160] Figures 1 to 4 The diagram illustrates the stacking sequence 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.

[0161] Figure 1 This 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.

[0162] Figure 3 and Figure 4 This illustrates the 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 transport layer 302, a light-emitting layer 304, an electron transport layer 305, and an electron injection layer 306, and according to Figure 4 The organic light-emitting element includes a hole injection layer 301, a hole transport layer 302, an electron blocking layer 303, a light-emitting layer 304, an electron transport layer 305, and an electron injection layer 306. However, the scope of this application is not limited to this layered structure, and layers other than the light-emitting layer may be excluded as needed, and other required functional layers may be added.

[0163] The organic material layer containing the compound of formula 1 may further contain other materials as needed.

[0164] In an organic light-emitting element according to one embodiment of this specification, materials other than those of chemical 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.

[0165] As anode materials, materials with relatively large work functions can be used, and transparent conductive oxides, metals, conductive polymers, etc., can be used. Specific examples of anode materials include: metals, such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides, such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides, such as ZnO:Al or SnO2:Sb; conductive polymers, such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, etc., but are not limited to these.

[0166] Materials with relatively small work functions can be used as cathode materials, including metals, metal oxides, and conductive polymers. 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, but are not limited to these.

[0167] As hole injection materials, 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-carbazolyl-9-ylphenyl)amine (TCTA), 4,4',4”-tris[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA) or 1,3,5-tris[4-(3-methylphenylanilino)phenyl]benzene (m-MTDAPB) as conductive polymers with solubility, such as polyaniline / dodecylbenzenesulfonic acid, poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate), polyaniline / camphorsulfonic acid, or polyaniline / poly(4-styrenesulfonate), etc.

[0168] As hole transport materials, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, etc., can be used, and low-molecular-weight or high-molecular-weight materials can also be used.

[0169] As an electron transport material, metal complexes of oxadiazole derivatives, anthraquinone dimethyl ether and its 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, etc., can be used, as well as polymeric and low-molecular-weight materials.

[0170] As an example of an electron-injected material, LiF is commonly used in this technology; however, this application is not limited to this.

[0171] 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. Furthermore, 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.

[0172] In one embodiment of this specification, an anthracene-containing compound may be used as the host material; however, the host material is not limited to this.

[0173] In one embodiment of this specification, a pyrene derivative containing a diamine can be used as a dopant material; however, the dopant material is not limited to this.

[0174] When mixing luminescent material substrates, substrates from the same series or different series can be mixed. For example, any two or more N-type or P-type substrate materials can be selected as the substrate material for the luminescent layer.

[0175] An organic light-emitting element according to one embodiment of this specification may be a top-emitting, bottom-emitting, or dual-emitting type, depending on the material used.

[0176] 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, etc., based on similar principles used in organic light-emitting elements.

[0177] 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.

[0178] [Preparation Example 1] Preparation of Compound 2

[0179]

[0180] 1) Preparation of compound 2-2

[0181] Methyl pyrrolidone (NMP) (100 mL) was introduced into 4-phenylnaphthyl-2-ol (A) (20 g, 0.090 mol, 1 equivalent), 1,3-dichloro-2-fluorobenzene (B) (18 g, 0.108 mol, 1.2 equivalent), and K₂CO₃ (25 g, 0.181 mol, 2 equivalent), and the mixture was stirred at 160 °C for 12 h. The reaction was terminated by introducing water, and the results were extracted with methylene chloride (MC) and water. The water was then removed with MgSO₄. The results were separated using a silica gel column to give compound 2-2 (14 g) in 42% yield.

[0182] 2) Preparation of compounds 2-3

[0183] Dimethylacetamide (DMA) (140 mL) was introduced into compound 2-2 (14 g, 0.038 mol, 1 equivalent), K₂CO₃ (7.9 g, 0.057 mol, 1.5 equivalent), palladium(II) acetate (Pd(OAc)₂) (0.4 g, 0.0019 mol, 0.05 equivalent), and tricyclohexylphosphine tetrafluoroborate (PCy₃HBF₄) (1.4 g, 0.0038 mol, 0.1 equivalent), and the mixture was stirred at 140 °C for 12 h. The reaction was terminated by introducing water, and the results were extracted with MC and water. The water was then removed with MgSO₄. The results were separated using a silica gel column to give compound 2-3 (8 g) in 63% yield.

[0184] 3) Preparation of compound 2

[0185] Tris-tert-butylphosphine (P(t-Bu)3) (0.5 g, 0.0024 mol, 0.1 equivalent) and toluene (80 mL) were introduced into compounds 2-3 (8 g, 0.024 mol, 1 equivalent), N-phenyl-[1,1'-biphenyl]-4-amine (D) (6.3 g, 0.025 mol, 1.05 equivalent), sodium tert-butoxide (NaOt-Bu) (3.4 g, 0.036 mol, 1.5 equivalent), and tris(dibenzylacetone)dipalladium (O) (Pd2(dba)3) (1.1 g, 0.0012 mol, 0.05 equivalent), and the mixture was stirred at 100 °C for 8 hours. The reaction was terminated by the introduction of water, and the results were extracted with MC and water. The water was then removed with MgSO4. The results were separated using a silica gel column to give compound 2 (8 g) in 61% yield.

[0186] [Preparation Example 2] Preparation of Compound 194

[0187]

[0188] 1) Preparation of compound 194-2

[0189] 1,4-Dioxane (150 mL) and H₂O (45 mL) were introduced into 1-phenylnaphth-2-yltrifluoromethanesulfonate (A) (15 g, 0.042 mol, 1 equivalent), (3-chloro-2-(methoxycarbonyl)phenyl)boronic acid (B) (10 g, 0.046 mol, 1.1 equivalent), K₂CO₃ (12.9 g, 0.094 mol, 2.2 equivalent), and tetrakis(triphenylphosphine)palladium(O)(Pd(PPh₃)₄) (2.4 g, 0.0021 mol, 0.005 equivalent), and the mixture was stirred at 100 °C for 6 h. The reaction was terminated by the introduction of water, and the results were extracted with MC and water. The water was then removed with MgSO₄. The results were separated using a silica gel column to give compound 194-2 (12 g) in 75% yield.

[0190] 2) Preparation of compound 194-3

[0191] Compound 194-2 (12 g, 0.032 mol, 1 equivalent) was dissolved in tetrahydrofuran (THF) (120 mL). Methyl magnesium bromide (3 M diethyl ether solution) (D) (32.2 mL, 0.096 mol, 3 equivalent) was slowly added at 0 °C, and the mixture was stirred at 60 °C for 6 h. The reaction was terminated by introducing water, and the results were extracted with MC and water. The water was then removed with MgSO4. Borontrifluoride diethyl etherate was added to the reactants dissolved in MC, and the mixture was stirred at room temperature (RT) for 4 h. The results were separated using a silica gel column to give compound 194-3 (9 g) in 79% yield.

[0192] 3) Preparation of compound 194

[0193] Toluene (80 mL) was introduced into compound 194-3 (9 g, 0.025 mol, 1 equivalent), N-phenyl-[1,1'-biphenyl]-4-amine (C) (6.5 g, 0.026 mol, 1.05 equivalent), sodium terbutoxide (NaOt-Bu) (3.7 g, 0.038 mol, 1.5 equivalent), Pd2(dba)3 (1.1 g, 0.0012 mol, 0.05 equivalent), and P(t-Bu)3 (0.5 g, 0.0024 mol, 0.1 equivalent), and the mixture was stirred at 100 °C for 8 hours. The reaction was terminated by introducing water, and the results were extracted with MC and water. The water was then removed with MgSO4. The results were separated using a silica gel column to give compound 194 (10 g) in 73% yield.

[0194] The compounds were synthesized in the same manner as in Preparation Example 1 or Preparation Example 2, except that intermediates A, B, C and D from Table 1 below were used instead of (A), (B), (C) and (D).

[0195] [Table 1]

[0196]

[0197]

[0198]

[0199]

[0200] The compounds were prepared in the same manner as in the preparation examples, and the synthesis identification results are shown in Tables 2 and 3. Table 2 shows the 1H NMR (CDCl3, 200 MHz) measurements, and Table 3 shows the FD-mass spectrometry (field desorption mass spectrometry: FD-Mass) measurements.

[0201] [Table 2]

[0202]

[0203] [Table 3]

[0204] compound FD-MS compound FD-MS 2 m / z = 537.21 16 m / z = 653.27 42 m / z = 613.24 50 m / z = 693.30 60 m / z = 817.33 138 m / z = 629.22 144 m / z = 669.25 194 m / z = 563.26 202 m / z = 639.29 212 m / z = 755.36 240 m / z = 679.32 256 m / z = 841.37 268 m / z = 763.32 272 m / z = 803.36 277 m / z = 853.33 289 m / z = 611.26 294 m / z = 763.32 340 m / z = 689.27 420 m / z = 715.32 454 m / z = 729.30 464 m / z = 729.30 473 m / z = 679.32 483 m / z = 627.26 495 m / z = 743.32

[0205] [Experimental Example]

[0206] <Experimental Example 1>

[0207] 1) Manufacturing of organic light-emitting elements

[0208] Comparative Example 1

[0209] A transparent indium tin oxide (ITO) electrode film obtained from organic light-emitting diode (OLED) glass (manufactured by Samsung-Corning Co., Ltd.) was continuously ultrasonically cleaned for 5 minutes each using trichloroethylene, acetone, ethanol, and distilled water. The transparent ITO electrode film was then stored in isopropanol and used. Next, the ITO substrate was mounted in the substrate folder of the vacuum deposition apparatus, and 4,4',4”-tris(N,N-(2-naphthyl)-aniline)triphenylamine (2-TNATA) was introduced into the cell of the vacuum deposition apparatus.

[0210]

[0211] Subsequently, the chamber is evacuated until a vacuum level of 10⁻⁶ Torr is achieved, and then 2-TNATA is evaporated by applying current to the unit to deposit a hole injection layer with a thickness of 600 angstroms on the ITO substrate. N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) is introduced into another unit in the vacuum deposition apparatus and evaporated by applying current to the unit to deposit a hole transport layer with a thickness of 300 angstroms on the hole injection layer.

[0212]

[0213] After forming the hole injection layer and hole transport layer as described above, a blue luminescent material with the following structure is deposited on them as the luminescent layer. Specifically, in one unit of the vacuum deposition apparatus, the blue luminescent host material H1 is vacuum deposited to a thickness of 200 angstroms, and the blue luminescent dopant material D1 is deposited on top of the host material with a 5% vacuum.

[0214]

[0215] Subsequently, a compound having the following structural formula E1 was deposited to a thickness of 300 angstroms as an electron transport layer.

[0216]

[0217] As the electron injection layer, lithium fluoride (LiF) was deposited to a thickness of 10 angstroms, and an Al cathode was used to a thickness of 1,000 angstroms, thus fabricating an OLED. Simultaneously, all the organic compounds required for OLED fabrication were purified by vacuum sublimation at 10⁻⁸ Torr to 10⁻⁶ Torr for each material used in OLED fabrication.

[0218] Comparative Examples 2 to 7 and Examples 1 to 24

[0219] The organic electroluminescent element was manufactured in the same manner as in Comparative Example 1, except that the compounds shown in Table 4 below were used instead of the NPB used in forming the hole transport layer in Comparative Example 1.

[0220]

[0221] 2) Evaluation of organic light-emitting elements

[0222] For each of the organic electroluminescent elements manufactured as described above, the electroluminescence (EL) properties were measured using an M7000 manufactured by McScience Inc., and using the measurement results, the lifetime measurement was performed using a McScience Inc. lifetime measurement system (M6000) at a standard luminance of 700 candela / m² (cd / m²). 2 T95 at that time.

[0223] The driving voltage, luminous efficiency, color coordinate (CIE) and lifetime of the blue organic light-emitting element manufactured according to this disclosure are shown in Table 4.

[0224] [Table 4]

[0225]

[0226]

[0227] As can be seen from the results in Table 4, compared with the comparative example, the organic light-emitting element using the hole transport layer material of the blue organic light-emitting element disclosed herein has a lower driving voltage and significantly improved luminous efficiency and lifetime.

[0228] When comparing the comparative examples in Table 4 with the compounds disclosed herein, they are similar in having arylamine groups; however, the difference lies in the presence of a fluorene group with a substituent. The fluorene group with a substituent inhibits the π-π stacking of the aromatic ring, thus preventing the degradation of the device properties caused by increasing the driving voltage of the organic light-emitting element. Therefore, it is believed that the compounds disclosed herein, using such derivatives, enhance hole transport properties or stability, thereby exhibiting superiority in all aspects, including driving voltage, efficiency, and lifetime.

[0229] <Experimental Example 2>

[0230] 1) Manufacturing of organic light-emitting elements

[0231] Comparative Example 8

[0232] A transparent indium tin oxide (ITO) electrode film obtained from organic light-emitting diode (OLED) glass (manufactured by Samsung-Corning Co., Ltd.) was continuously ultrasonically cleaned for 5 minutes each using trichloroethylene, acetone, ethanol, and distilled water. The transparent ITO electrode film was then stored in isopropanol and used. Next, the ITO substrate was mounted in the substrate folder of the vacuum deposition apparatus, and 4,4',4”-tris(N,N-(2-naphthyl)-aniline)triphenylamine (2-TNATA) was introduced into the cell of the vacuum deposition apparatus.

[0233]

[0234] Subsequently, the chamber is evacuated until a vacuum level of 10⁻⁶ Torr is achieved, and then 2-TNATA is evaporated by applying current to the unit to deposit a hole injection layer with a thickness of 600 angstroms on the ITO substrate. N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) is introduced into another unit in the vacuum deposition apparatus and evaporated by applying current to the unit to deposit a hole transport layer with a thickness of 300 angstroms on the hole injection layer.

[0235]

[0236] After forming the hole injection layer and hole transport layer as described above, a blue luminescent material with the following structure is deposited on them as the luminescent layer. Specifically, in one unit of the vacuum deposition apparatus, the blue luminescent host material H1 is vacuum deposited to a thickness of 200 angstroms, and the blue luminescent dopant material D1 is deposited on top of the host material with a 5% vacuum.

[0237]

[0238] Subsequently, a compound with the following structural formula E1 was deposited to a thickness of 300 angstroms as an electron transport layer.

[0239]

[0240] As the electron injection layer, lithium fluoride (LiF) was deposited to a thickness of 10 angstroms, and an Al cathode was used to a thickness of 1,000 angstroms, thus fabricating an OLED. Simultaneously, all the organic compounds required for OLED fabrication were purified by vacuum sublimation at 10⁻⁸ Torr to 10⁻⁶ Torr for each material used in OLED fabrication.

[0241] Comparative Examples 9 to 14 and Examples 25 to 48

[0242] The organic electroluminescent element was fabricated in the same manner as in Comparative Example 8, except that after forming the hole transport layer NPB to a thickness of 250 angstroms in Comparative Example 8, an electron blocking layer to a thickness of 50 angstroms was formed on the hole transport layer using the compounds described in Table 5 below.

[0243]

[0244] 2) Evaluation of organic light-emitting elements

[0245] For each of the organic electroluminescent elements manufactured as described above, the electroluminescence (EL) properties were measured using an M7000 manufactured by Maxis Corporation, and using the measurement results, the T95 at a standard luminance of 6000 candela / m² was measured using a lifetime measurement system (M6000) manufactured by Maxis Corporation.

[0246] The driving voltage, luminous efficiency, color coordinates (CIE), and lifetime of the blue organic light-emitting element manufactured according to this disclosure are shown in Table 5 below.

[0247] [Table 5]

[0248]

[0249] As can be seen from the results in Table 5, compared with the comparative example, the organic light-emitting element using the electron blocking layer material of the blue organic light-emitting element disclosed herein has a lower driving voltage and significantly improved luminous efficiency and lifetime.

[0250] When electrons pass through the hole transport layer and move to the anode without binding in the emissive layer, the efficiency and lifetime of OLEDs decrease. When a compound with a high LUMO energy level is used as an electron blocking layer to prevent this phenomenon, the electrons passing through the emissive layer and moving to the anode are blocked by the energy barrier of the electron blocking layer. Therefore, holes and electrons are highly likely to form excitons, thereby increasing the likelihood of light emission in the emissive layer. Thus, the compound disclosed in this paper is considered to offer superior performance in all aspects, including driving voltage, efficiency, and lifetime.

[0251] Specifically, it is identified that when an amine derivative is used as a hole transport layer in the compound having Formula 1 of this application, the non-shared electron pairs of the amine improve the flow of holes, thereby enhancing the hole transport capability of the hole transport layer. Furthermore, when used as an electron blocking layer, it suppresses the degradation of the hole transport material caused by electron intrusion into the hole transport layer. In addition, the planarity and glass transition temperature of the amine derivative are increased due to the bonding between the substituents with enhanced hole properties and the amine sites, which increases the thermal stability of the compound.

[0252] Furthermore, it was found that by adjusting the band gap and the T1 (energy level value in the triplet state) value, the hole transport capability was enhanced, and the molecular stability was also increased. As a result, the driving voltage of the device was reduced, the optical efficiency was enhanced, and the lifetime properties of the device were improved by the thermal stability of the compound.

Claims

1. A compound having the following chemical formula 1: [Chemical Formula 1] In chemical formula 1, X is O; S; or CR'R". R' and R" are each independently a substituted or unsubstituted C1 to C10 alkyl group; or a substituted or unsubstituted C6 to C10 aryl group. L11 and L12 are each independently direct bonds; or substituted or unsubstituted C6 to C10 arylene groups. R11 and R12 are each independently a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group. L1 and L2 are each independently a direct bond; or a phenylene group. Ar is a C6 to C20 aryl group; or a C2 to C20 heteroaryl group containing O or S. R1 is hydrogen; or deuterium. r is an integer from 0 to 8, and when r is 2 or greater than 2, R1 is either the same or different from each other. The term "substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of: deuterium; halogen; cyano; C1 to C60 alkyl; C2 to C60 alkenyl; C2 to C60 alkynyl; C3 to C60 cycloalkyl; C2 to C60 heterocycloalkyl; C6 to C60 aryl; and C2 to C60 heteroaryl, or substituted with a substituent connected to two or more substituents selected from the above substituents, or unsubstituted.

2. The compound according to claim 1, wherein chemical formula 1 is represented by the following chemical formula 2: [Chemical Formula 2] In chemical formula 2, Each substituent has the same definition as in Formula 1.

3. The compound according to claim 1, wherein chemical formula 1 is represented by any of the following compounds:

4. An organic light-emitting element, comprising: First electrode; Second electrode; and An organic material layer is disposed between the first electrode and the second electrode. The organic material layer thereof comprises the compound as described in any one of claims 1 to 3.

5. The organic light-emitting element according to claim 4, wherein the organic material layer comprises a hole transport layer, and the hole transport layer contains the compound.

6. The organic light-emitting element according to claim 4, wherein the organic material layer comprises an electron blocking layer, and the electron blocking layer contains the compound.

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