Compound and organic light-emitting device comprising same

Abstract

The present specification relates to a compound of chemical formula 1 and an organic light-emitting device comprising the same, the compound of chemical formula 1 being a compound in which anthracene, which plays a key role as a core when the compound serves as a blue fluorescent host compound, is substituted with deuterium, and the compound of chemical formula 1 being used in an organic light-emitting device, and therefore, device characteristics can be improved, for example, such that the device can have low driving voltage, excellent efficiency characteristics, or excellent lifespan characteristics.

Description

TECHNICAL FIELD

[0001] This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0046051, filed on April 7, 2023, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

[0002] The present specification relates to a compound and an organic light emitting device comprising the same. BACKGROUND

[0003] An organic light emitting phenomenon generally refers to a phenomenon that electric energy is converted into light energy using an organic material. An organic light emitting device utilizing the organic light emitting phenomenon typically has a structure including a positive electrode, a negative electrode, and an organic material layer therebetween. Here, the organic material layer has a multi-layer structure composed of different materials in many cases to improve efficiency and stability of the organic light emitting device, and can be composed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In such a structure of the organic light emitting device, if a voltage is applied between the two electrodes, holes are injected from the positive electrode into the organic material layer and electrons are injected from the negative electrode into the organic material layer, a exciton is formed when the injected holes and electrons meet each other, and light is emitted when the exciton falls to a ground state.

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

[0005] TECHNICAL PROBLEM

[0006] The present specification provides a compound and an organic light emitting device comprising the same.

[0007] TECHNICAL SOLUTION

[0008] The present specification provides a compound of the following Chemical Formula 1.

[0009] [Chemical Formula 1]

[0010]

[0011] In Chemical Formula 1,

[0012] R1 to R8 are the same as or different from each other, and each is independently deuterium; a substituted or unsubstituted aryl; or a substituted or unsubstituted heteroaryl,

[0013] R9 and R 10 are the same as or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted alkyl; a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; or a substituted or unsubstituted naphthyl,

[0014] m is an integer of 1 to 4,

[0015] n is an integer of 1 to 3,

[0016] Ar1is phenyl unsubstituted or substituted with deuterium; or naphthyl unsubstituted or substituted with one or more of deuterium and alkyl, and

[0017] Ar2is biphenyl unsubstituted or substituted with deuterium or alkyl; terphenyl unsubstituted or substituted with deuterium or alkyl; naphthyl unsubstituted or substituted with deuterium or alkyl; phenylnaphthyl unsubstituted or substituted with deuterium or alkyl; or naphthylphenyl unsubstituted or substituted with deuterium or alkyl.

[0018] Further, one exemplary embodiment of the present specification provides an organic light-emitting device including: a first electrode; a second electrode; and an organic material layer having one or more layers disposed between the first electrode and the second electrode, wherein one or more layers of the organic material layer comprise the above-described compound.

[0019] Advantages

[0020] When the compound according to one exemplary embodiment of the present application functions as a blue fluorescent host compound, the anthracene that plays a key role as a core is substituted with deuterium to extract binding energy, and when included in an organic light-emitting device, the compound can improve device characteristics, for example, enabling the device to have a low driving voltage, excellent efficiency characteristics, or excellent lifespan characteristics. BRIEF DESCRIPTION OF DRAWINGS

[0021] Figure 1 and Figure 2 One example of an organic light-emitting device according to one exemplary embodiment of the present specification is illustrated.

[0022] Figure 3 MS chart for Compound A.

[0023] [Explanation of Reference Numbers and Symbols]

[0024] 1: Substrate

[0025] 2: First electrode

[0026] 3: Second electrode

[0027] 4: Organic material layer

[0028] 5: Hole injection layer

[0029] 6: Hole transport layer

[0030] 7: Electron blocking layer

[0031] 8: Emission layer

[0032] 9: Hole blocking layer

[0033] 10: Electron injection and transport layer DETAILED DESCRIPTION

[0034] Hereinafter, the present specification will be described in more detail.

[0035] Examples of substituents in the present specification will be described below, but are not limited thereto.

[0036] In the present specification, means a moiety to be connected.

[0037] The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent, and the position to be substituted is not limited as long as the position is a position where a hydrogen atom is replaced (i.e., a position where a substituent can be replaced), and when two or more hydrogen atoms are replaced, two or more substituents can be the same as or different from each other.

[0038] In the present specification, the term "substituted or unsubstituted" means substituted with one or more substituents selected from deuterium; a halogen group; a cyano group; an alkyl group; a cycloalkyl group; an alkoxy group; an aryloxy group; an alkylthio group; an arylthio group; an alkenyl group; a haloalkyl group; a haloalkoxy group; an arylalkyl group; a silyl group; a boron group; an amine group; an aryl group; and a heterocyclic group, a substituent substituted with two or more substituents exemplified from among the substituents are connected to each other, or no substituent.

[0039] In the present specification, the fact that two or more substituents are connected to each other means that a hydrogen of any substituent is connected to another substituent. For example, when two substituents are connected to each other, a phenyl group and a naphthyl group can be connected to each other to form a substituent In addition, the case where three substituents are connected to each other includes not only the case where (substituent 1)-(substituent 2)-(substituent 3) are sequentially connected to each other, but also the case where (substituent 2) and (substituent 3) are connected to (substituent 1). For example, a phenyl group, a naphthyl group, and an isopropyl group can be connected to each other to become a substituent The above definition is equally applicable to the case where four or more substituents are connected to each other.

[0040] In the present specification, examples of the halogen group include fluorine, chlorine, bromine, or iodine.

[0041] In the present specification, an alkyl group can be linear or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 1 to 30. Specific examples thereof include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group,

[0042] n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl,

[0043] cyclohexylmethyl, octyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isoheptyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

[0044] In the present specification, a cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, and specific examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentyl group, a 2,3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 2,3-dimethylcyclohexyl group, a 3,4,5-trimethylcyclohexyl group, a 4-t-butylcyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.1]octyl group, a norbornyl group, and the like, but are not limited thereto.

[0045] In the present specification, an alkoxy group can be linear, branched, or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30. Specific examples thereof include a methoxy group, an ethoxy group, an n-propoxy group, an iso-propoxy group, an n-butoxy group, an iso-butoxy group, a t-butoxy group, a sec-butoxy group, an n-pentoxy group, a neopentoxy group, an iso-pentoxy group, an n-hexyloxy group, a 3,3-dimethylbutoxy group, a 2-ethylbutoxy group, an n-octyloxy group, an n-nonyloxy group, an n-decyloxy group, a benzyloxy group, a p-methylbenzyloxy group, and the like, but are not limited thereto.

[0046] In the present specification, an alkenyl group can be linear or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 2 to 30. Specific examples thereof include an ethenyl group, a 1-propenyl group, an iso-propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 3-methyl-1-butenyl group, a 1,3-butanedienyl group, an allyl group, a 1-phenylethen-1-yl group, a 2-phenylethen-1-yl group, a 2,2-diphenylethen-1-yl group, a 2-phenyl-2-(naphthyl-1-yl)ethen-1-yl group, a 2,2-bis(diphenyl-1-yl)ethen-1-yl group, a stilbenyl group, a styryl group, and the like, but are not limited thereto.

[0047] In the present specification, a haloalkyl group means that, in the definition of an alkyl group, at least one halogen group is substituted for hydrogen in the alkyl group.

[0048] In the present specification, haloalkoxy means that, in the definition of alkoxy, at least one halogen group is substituted for hydrogen in the alkoxy group.

[0049] In the present specification, an aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group can be monocyclic or polycyclic.

[0050] When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30. Specific examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and the like, but are not limited thereto.

[0051] When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 10 to 30. Specific examples of the polycyclic aryl group include a naphthyl group, an anthryl group, a phenanthryl group, a triphenylenyl group, a pyrenyl group, a phenalenyl group, a perylenyl group, a fluorenyl group, and the like, but are not limited thereto.

[0052] In the present specification, a fluorenyl group can be substituted, and adjacent groups can be bonded to each other to form a ring.

[0053] Examples of the case where the fluorenyl group is substituted include

[0054] and the like, but are not limited thereto.

[0055] In the present specification, an "adjacent" group can mean a substituent that substitutes an atom directly connected to an atom substituted with a corresponding substituent, a substituent located spatially closest to the corresponding substituent, or another substituent that substitutes an atom substituted with the corresponding substituent. For example, two substituents that substitute the ortho position of a benzene ring and two substituents that substitute the same carbon in an aliphatic ring can be interpreted as groups that are "adjacent" to each other.

[0056] In the present specification, an arylalkyl group means that an alkyl group is substituted with an aryl group, and examples of the above-described aryl group and alkyl group can be applied to the aryl group and alkyl group of the arylalkyl group.

[0057] In the present specification, an aryloxy group means that, in the definition of an alkoxy group, the alkyl group in the alkoxy group is replaced with an aryl group, and examples of the aryloxy group include a phenoxy group, a p-tolyloxy group, an m-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6-trimethylphenoxy group, a p-t-butylphenoxy group, a 3-biphenyloxy group, a 4-biphenyloxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 4-methyl-1-naphthyloxy group, a 5-methyl-2-naphthyloxy group, a 1-anthryloxy group, a 2-anthryloxy group, a 9-anthryloxy group, a 1-phenanthryloxy group, a 3-phenanthryloxy group, a 9-phenanthryloxy group, and the like, but are not limited thereto.

[0058] ​In the present specification, the alkyl group in the alkylthio group is the same as the above examples of the alkyl group. Specific examples of the alkylthio group include a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group, an octylthio group, and the like, but are not limited thereto.

[0059] In the present specification, the aryl group in the arylthio group is the same as the above examples of the aryl group. Specific examples of the arylthio group include a phenylthio group, a 2-methylphenylthio group, a 4-tert-butylphenylthio group, and the like, but are not limited thereto.

[0060] In the present specification, the heterocyclic group contains one or more atoms other than carbon, that is, one or more heteroatoms, and specifically, the heteroatoms can include one or more atoms selected from O, N, Se, S, and the like, and include an aromatic heterocyclic group or an aliphatic heterocyclic group. The aromatic heterocyclic group can be represented by a heteroaryl group. The number of carbon atoms of the heterocyclic group is not particularly limited, but is preferably 2 to 30, and the heterocyclic group can be monocyclic or polycyclic. Examples of the heterocyclic group include a thienyl group, a furanyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, oxazolyl group, oxadiazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazinyl group, a triazolyl group, an acridyl group, a pyridazinyl group, a pyrazinyl group, a quinolyl group, a quinazolyl group, a quinoxalyl group, a phtalazinyl group, a pyridopyrimidyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinolyl group, an indolyl group, a carbazolyl group, a benz oxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothiophenyl group, a dibenzothiophenyl group, a benzofuranyl group, a phenanthridyl group, a phenanthrolinyl group, an iso oxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothiophenyl group, a dibenzothiophenyl group, a benzofuranyl group, a phenanthridyl group, a phenanthrolinyl group, an iso oxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothiophenyl group, a dibenzothiophenyl group, a benzofuranyl group, a phenanthridyl group, a phenanthrolinyl group, an iso oxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothiophenyl group, a dibenzothiophenyl group, a benzofuranyl group, a phenanthridyl group, a phenanthrolinyl group, an iso

[0061] In the present specification, the silyl group can be an alkylsilyl group, an arylsilyl group, an alkylarylsilyl group, a heteroarylsilyl group, and the like. The above examples of the alkyl group can be applied to the alkyl group in the alkylsilyl group, the above examples of the aryl group can be applied to the aryl group in the arylsilyl group, the examples of the alkyl group and the aryl group can be applied to the alkyl group and the aryl group in the alkylarylsilyl group, and the examples of the heterocyclic group can be applied to the heteroaryl group in the heteroarylsilyl group.

[0062] In the present specification, the boron group can be -BY 100 Y 101 , and Y 100 and Y 101They may be the same as or different from each other, and may be independently selected from hydrogen; deuterium; halogen; nitrile group; substituted or unsubstituted monocyclic or polycyclic cycloalkyl groups having 3 to 30 carbon atoms; substituted or unsubstituted straight-chain or branched alkyl groups having 1 to 30 carbon atoms; substituted or unsubstituted monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms; and substituted or unsubstituted monocyclic or polycyclic heterocyclic groups having 2 to 30 carbon atoms. Specific examples of boron groups include, but are not limited to, dimethylboryl, diethylboryl, tert-butylmethylboryl, diphenylboryl, etc.

[0063] In this specification, the amino group may be selected from -NH2, alkylamino, N-alkylarylamino, arylamino, N-arylheteroarylamino, N-alkylheteroarylamino, and heteroarylamino, and its number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of amino groups include methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, naphthylamino, biphenylamino, anthraceneamino, 9-methyl-anthraylamino, diphenylamino, xylylamino, N-phenyltolylamino, N-phenylbiphenylamino, N-phenylnaphthylamino, N-biphenylnaphthylamino, N-naphthylfluorenylamino, N-phenylphenanthreneamino, N-biphenylphenanthreneamino, N-phenylfluorenylamino, N-phenyltriphenylamino, N-phenanthrenefluorenylamino, N-biphenylfluorenylamino, etc., but are not limited thereto.

[0064] In this specification, N-alkylarylamine means that the N of the amino group is replaced by an alkyl or aryl amino group. The alkyl and aryl groups in N-alkylarylamine are the same as those in the examples of alkyl and aryl groups described above.

[0065] In this specification, N-arylheteroarylamine means that the N-amino group is substituted with an aryl or heteroaryl amino group. The aryl and heteroaryl groups in N-arylheteroarylamine are the same as those in the examples of aryl and heterocyclic groups described above.

[0066] In this specification, N-alkylheteroarylamine means that the N of the amino group is replaced by an alkyl or heteroaryl amino group. The alkyl and heteroaryl groups in N-alkylheteroarylamine are the same as those in the examples of alkyl and heterocyclic groups described above.

[0067] In this specification, examples of alkylamine groups include substituted or unsubstituted monoalkylamine groups or substituted or unsubstituted dialkylamine groups. The alkyl group in an alkylamine group can be a straight-chain or branched alkyl group. An alkylamine group containing two or more alkyl groups can contain a straight-chain alkyl group, a branched alkyl group, or both a straight-chain alkyl group and a branched alkyl group. For example, the alkyl group in an alkylamine group can be selected from the above-described examples of alkyl groups.

[0068] In this specification, examples of heteroarylamines include substituted or unsubstituted mono-heteroarylamines or substituted or unsubstituted di-heteroarylamines. Heteroarylamines comprising two or more heteroaryl groups may include monocyclic heteroaryl, polycyclic heteroaryl, or both. For example, the heteroaryl groups in a heteroarylamine may be selected from the above-described examples of heterocyclic groups.

[0069] In this specification, the alkyl group in N-alkylarylamine, alkylthio, and N-alkylheteroarylamine is the same as the alkyl group described above. Specific examples of alkylthio groups include, but are not limited to, methylthio, ethylthio, tert-butylthio, hexylthio, octylthio, etc.

[0070] In this specification, the aryl groups in aryloxy, arylthio, N-arylalkylamine, and N-arylheteroarylamine are the same as those described above. Specifically, examples of aryloxy groups include phenoxy, p-tolyloxy, m-tolyloxy, 3,5-dimethyl-phenoxy, 2,4,6-trimethylphenoxy, p-tert-butylphenoxy, 3-biphenoxy, 4-biphenoxy, 1-naphthoxy, 2-naphthoxy, 4-methyl-1-naphthoxy, 5-methyl-2-naphthoxy, 1-anthraoxy, 2-anthraoxy, 9-anthraoxy, 1-phenanthoxy, 3-phenanthoxy, 9-phenanthoxy, etc., and examples of arylthio groups include phenylthio, 2-methylphenylthio, 4-tert-butylphenylthio, etc., but the examples are not limited thereto.

[0071] In this specification, the hydrocarbon cyclogroup can be an aromatic hydrocarbon cyclogroup, an aliphatic hydrocarbon cyclogroup, or a fused cyclogroup of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and can be selected from examples of cycloalkyl, aryl, and combinations thereof. Examples of hydrocarbon cyclogroups include phenyl, cyclohexyl, adamantyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.1]octyl, tetrahydronaphthyl, tetrahydroanthrayl, 1,2,3,4-tetrahydro-1,4-bridged methylenenaphthyl, 1,2,3,4-tetrahydro-1,4-bridged ethylnaphthyl, spirocyclopentanefluorenyl, spiroadamantanefluorenyl, spirocyclohexanefluorenyl, etc., but are not limited thereto.

[0072] In this specification, the meaning of "adjacent" in "bonded with adjacent groups to form a ring" is as described above, and "ring" means a substituted or unsubstituted hydrocarbon ring; or a substituted or unsubstituted heterocycle.

[0073] In this specification, aliphatic heterocycle means an aliphatic ring containing one or more heteroatoms. Furthermore, aliphatic heterocycle means any heterocycle excluding aromatic heterocycles, and a heterocycle containing a double bond but not being aromatic is an aliphatic heterocycle. Examples of aliphatic heterocycles include ethylene oxide, tetrahydrofuran, and 1,4-di(2 ... alkyl, pyrrolidine, piperidine, morpholine, oxepane, azocane, thiocane, tetrahydronaphthothiophene, tetrahydronaphthofuran, tetrahydrobenzothiophene, tetrahydrobenzofuran, and the like, but are not limited thereto.

[0074] In the present specification, an aliphatic heterocycle (group) means an aliphatic cycle (group) containing one or more heteroatoms. In addition, an aliphatic heterocycle (group) means any heterocycle (group) excluding an aromatic heterocycle (group), and a heterocycle (group) containing a double bond but not aromatic is an aliphatic heterocycle (group).

[0075] In the present specification, examples of an aliphatic cycle, or a fused heterocycle of an aromatic cycle and an aliphatic cycle include tetrahydronaphthothiophene, tetrahydronaphthofuran, and the like, but are not limited thereto.

[0076] In the present specification, phenylnaphthyl means substituted with phenyl in naphthyl, and naphthylphenyl means substituted with naphthyl in phenyl.

[0077] Unless defined otherwise in the present specification, all technical and scientific terms used in the present specification have the same meaning as commonly understood by one of ordinary skill in the art to which this application belongs. Although methods and materials similar or equivalent to those described in the present specification can be used in the practice or testing of the present application, suitable methods and materials are described below. All publications, patent applications, patents, and other references mentioned in the present specification are incorporated by reference in their entirety, and in the case of conflict, the present specification, including definitions, will control. In addition, the materials, methods, and examples are illustrative only and not intended to be limiting.

[0078] Hereinafter, the compound of Chemical Formula 1 will be described in detail.

[0079] According to one exemplary embodiment of the present specification, R1 to R8 of Chemical Formula 1 are the same as or different from each other, and each is independently deuterium; aryl which is unsubstituted or substituted with deuterium; or heteroaryl which is unsubstituted or substituted with deuterium.

[0080] According to one exemplary embodiment of the present specification, R9 and R 10 are the same as or different from each other, and each is independently hydrogen; deuterium; alkyl which is unsubstituted or substituted with deuterium; phenyl which is unsubstituted or substituted with deuterium; biphenyl which is unsubstituted or substituted with deuterium; or naphthyl which is unsubstituted or substituted with deuterium.

[0081] According to one exemplary embodiment of the present specification, Ar1 of Chemical Formula 1 is phenyl which is unsubstituted or substituted with deuterium; or naphthyl which is unsubstituted or substituted with one or more of deuterium or alkyl.

[0082] According to an exemplary embodiment of the present specification, Ar2 of Chemical Formula 1 is a biphenyl group which is not substituted or substituted with deuterium; a terphenyl group which is not substituted or substituted with deuterium; a naphthyl group which is not substituted or substituted with deuterium; or a phenyl naphthyl group which is not substituted or substituted with deuterium; or a naphthyl phenyl group which is not substituted or substituted with deuterium.

[0083] According to an exemplary embodiment of the present specification, R1 to R8 of Chemical Formula 1 are all deuterium.

[0084] According to an exemplary embodiment of the present specification, R9 and R 10 are the same as or different from each other, and each is independently hydrogen; or deuterium.

[0085] According to an exemplary embodiment of the present specification, R9 and R 10 are all deuterium.

[0086] According to an exemplary embodiment of the present specification, R9 and R 10 are one or more of deuterium.

[0087] According to an exemplary embodiment of the present specification, Ar1 of Chemical Formula 1 is substituted with one or more deuterium.

[0088] According to an exemplary embodiment of the present specification, Ar2 of Chemical Formula 1 is substituted with one or more deuterium.

[0089] According to an exemplary embodiment of the present specification, Ar1 of Chemical Formula 1 is a phenyl group having a deuterium substitution rate of 40% or more.

[0090] According to an exemplary embodiment of the present specification, Ar1 of Chemical Formula 1 is a phenyl group which is all substituted with deuterium.

[0091] According to an exemplary embodiment of the present specification, Ar1 of Chemical Formula 1 is a naphthyl group having a deuterium substitution rate of 40% or more.

[0092] According to an exemplary embodiment of the present specification, Ar1 of Chemical Formula 1 is a naphthyl group which is all substituted with deuterium.

[0093] According to an exemplary embodiment of the present specification, Ar2 of Chemical Formula 1 is a 1-naphthyl group which is substituted or not substituted.

[0094] According to an exemplary embodiment of the present specification, Ar2 of Chemical Formula 1 is a 2-naphthyl group which is substituted or not substituted.

[0095] According to an exemplary embodiment of the present specification, Ar2 of Chemical Formula 1 is any one of the following Chemical Formulas Ar2-1 to Ar2-8.

[0096]

[0097] in Chemical Formulae Ar2-1 to Ar2-8,

[0098] R', R", and R'" are the same as or different from each other and each is independently hydrogen; deuterium; or a substituted or unsubstituted alkyl,

[0099] x1 is an integer of 1 to 3, x2 is an integer of 1 to 4, x3 is an integer of 1 to 6, x4 is an integer of 1 to 7, y1 is an integer of 1 to 4, y2 is an integer of 1 to 5, y3 is an integer of 1 to 7, and z1 is an integer of 1 to 5, and

[0100] means a moiety to be connected.

[0101] According to one exemplary embodiment of the present specification, Chemical Formula 1 is any one of the following Chemical Formulae 1-1 to 1-3.

[0102] [Chemical Formula 1-1]

[0103]

[0104] [Chemical Formula 1-2]

[0105]

[0106] [Chemical Formula 1-3]

[0107]

[0108] in Chemical Formulae 1-1 to 1-3,

[0109] R1to R 10 , m, n, and Ar2are the same as the definitions in Chemical Formula 1, and

[0110] R 11 to R 17 are the same as or different from each other and each is independently hydrogen or deuterium.

[0111] According to one exemplary embodiment of the present specification, Chemical Formula 1 is any one of Chemical Formulae 2-1 to 2-3.

[0112] [Chemical Formula 2-1]

[0113]

[0114] [Chemical Formula 2-2]

[0115]

[0116] [Chemical Formula 2-3]

[0117]

[0118] In Chemical Formulae 2-1 to 2-3,

[0119] R1to R 10 , m, n, and Ar2are the same as the definitions in Chemical Formula 1, and

[0120] R 11 to R 15 are the same as or different from each other, and each is independently hydrogen or deuterium.

[0121] According to one exemplary embodiment of the present specification, Chemical Formula 1 is any one of Chemical Formulae 2-4 to 2-6.

[0122] [Chemical Formula 2-4]

[0123]

[0124] [Chemical Formula 2-5]

[0125]

[0126] [Chemical Formula 2-6]

[0127]

[0128] In Chemical Formulae 2-4 to 2-6,

[0129] R1to R 10 , m, n, and Ar2are the same as the definitions in Chemical Formula 1, and

[0130] R 11 to R 17 are the same as or different from each other, and each is independently hydrogen or deuterium.

[0131] According to one exemplary embodiment of the present specification, Chemical Formula 1 is any one of Chemical Formulae 2-7 to 2-9.

[0132] [Chemical Formula 2-7]

[0133]

[0134] [Chemical Formula 2-8]

[0135]

[0136] [Chemical Formula 2-9]

[0137]

[0138] In Chemical Formulae 2-7 to 2-9,

[0139] R1to R 10 , m, n, and Ar2are the same as defined in Chemical Formula 1, and

[0140] R 11 to R 17 are the same as or different from each other, and each is independently hydrogen or deuterium.

[0141] According to one exemplary embodiment of the present specification, Chemical Formula 1 is any one of Chemical Formulae 3-1 to 3-12.

[0142]

[0143]

[0144] In Chemical Formulae 3-1 to 3-12,

[0145] R1to R 10 , m, and n are the same as defined in Chemical Formula 1,

[0146] R 11 to R 17 are the same as or different from each other, and each is independently hydrogen or deuterium,

[0147] R' is hydrogen; deuterium; or an alkyl group, and

[0148] x3is an integer of 1 to 6, and x4is an integer of 1 to 7.

[0149] According to one exemplary embodiment of the present specification, Chemical Formula 1 is any one of Chemical Formulae 4-1 to 4-12.

[0150]

[0151]

[0152]

[0153] In Chemical Formulae 4-1 to 4-12,

[0154] R1to R 10 , m, and n are the same as defined in Chemical Formula 1,

[0155] R 11 to R 17 are the same as or different from each other, and each is independently hydrogen or deuterium,

[0156] R', R", and R'" are the same as or different from each other, and each is independently hydrogen; deuterium; or an alkyl group, and

[0157] x1 is an integer of 1 to 3, x2 is an integer of 1 to 4, y1 is an integer of 1 to 4, y2 is an integer of 1 to 5, y3 is an integer of 1 to 7, and z1 is an integer of 1 to 5.

[0158] According to one exemplary embodiment of the present specification, R1 to R8 of Chemical Formula 1 are all deuterium.

[0159] According to one exemplary embodiment of the present specification, R9 and R 10 are all deuterium.

[0160] According to one exemplary embodiment of the present specification, Ar1 of Chemical Formula 1 is a phenyl group which is all substituted with deuterium; or a naphthyl group which is all substituted with deuterium.

[0161] According to one exemplary embodiment of the present specification, R', R", and R'" of Chemical Formulae Ar2-1 to Ar2-8 are all deuterium.

[0162] According to one exemplary embodiment of the present specification, R 11 to R 17 of Chemical Formulae 1-1 to 1-3 are all deuterium.

[0163] According to one exemplary embodiment of the present specification, Ar2 of Chemical Formula 1 is a substituted or unsubstituted 1-naphthyl group.

[0164] According to one exemplary embodiment of the present specification, Ar2 of Chemical Formula 1 is a substituted or unsubstituted 2-naphthyl group.

[0165] According to one exemplary embodiment of the present specification, the deuterium substitution rate of Chemical Formula 1 is 10% or more.

[0166] According to one exemplary embodiment of the present specification, the deuterium substitution rate of Chemical Formula 1 is 30% or more.

[0167] According to one exemplary embodiment of the present specification, the deuterium substitution rate of Chemical Formula 1 is 40% or more.

[0168] According to one exemplary embodiment of the present specification, the deuterium substitution rate of Chemical Formula 1 is 50% or more.

[0169] According to one exemplary embodiment of the present specification, the deuterium substitution rate of Chemical Formula 1 is 60% or more.

[0170] According to one exemplary embodiment of the present specification, the deuterium substitution rate of Chemical Formula 1 is 70% or more.

[0171] According to one exemplary embodiment of the present specification, the deuterium substitution rate of Chemical Formula 1 is 80% or more.

[0172] According to one exemplary embodiment of the present specification, the deuterium substitution rate of Chemical Formula 1 is 90% or more.

[0173] According to one exemplary embodiment of the present specification, the deuterium substitution rate of Chemical Formula 1 is 100%.

[0174] According to one exemplary embodiment of the present specification, when Chemical Formula 1 contains deuterium, the following effects exist. Specifically, the physical and chemical properties related to deuterium (for example, the length of a chemical bond) are different from those of hydrogen, since the stretching amplitude of a C-D bond is smaller than that of a C-H bond, the van der Waals radius of deuterium is smaller than that of hydrogen, and in general, a C-D bond can show shorter and stronger than a C-H bond. Therefore, when the hydrogen at the substitutable position in Chemical Formula 1 is replaced with deuterium, the energy of the ground state is lowered, and the bond length between deuterium and carbon is shortened, thereby causing the molecular hard-core volume to decrease, and thus the polarizability can be lowered, and the film volume can be increased by weakening the intermolecular interaction. In addition, these properties can have the effect of reducing the crystallinity of the thin film (i.e., producing an amorphous state) and in general, can be effective for improving the lifespan and driving characteristics of an organic light-emitting device, and the heat resistance can be improved compared to the organic light-emitting device in the related art.

[0175] In the present specification, "contains deuterium", "deuterated", or "deuterated" means that the hydrogen at the substitutable position of the compound is replaced with deuterium.

[0176] In the present specification, "over-deuterated" means a compound or a group in which all the hydrogens in the molecule are replaced with deuterium, and has the same meaning as "100% deuterated".

[0177] In the present specification, "X% deuterated", "X% deuterium degree", or "X% deuterium substitution rate" means that X% of the hydrogens at the substitutable position in the corresponding structure are replaced with deuterium. For example, when the corresponding structure is dibenzofuran, dibenzofuran that is "25% deuterated", "25% deuterium degree" of dibenzofuran, or "25% deuterium substitution rate" of dibenzofuran means that 2 of the 8 hydrogens at the substitutable position of dibenzofuran are replaced with deuterium.

[0178] In the present specification, the "deuterium degree" or "deuterium substitution rate" can be determined by a known method such as nuclear magnetic resonance spectroscopy (HNMR), thin layer chromatography / mass spectrometry (TLC / MS), or gas chromatography / mass spectrometry (GC / MS). 1 HNMR), thin layer chromatography / mass spectrometry (TLC / MS), or gas chromatography / mass spectrometry (GC / MS).

[0179] Specifically, when nuclear magnetic resonance spectroscopy (HNMR) is used, the deuterium degree or the deuterium substitution rate can be calculated by the following equation 1. 1When analyzing "degree of deuteration" or "rate of deuteration" using ¹H NMR, the degree of deuteration or rate of deuteration can be determined by adding dimethylformamide (DMF) as an internal standard. 1 The integral of the total peak is calculated by the integration ratio in H NMR.

[0180] Furthermore, when analyzing "degree of deuteration" or "deuteration substitution rate" by thin-layer chromatography / mass spectrometry (TLC / MS), the substitution rate can be calculated based on the maximum (median) value of the molecular weight distribution at the end of the reaction. For example, when analyzing the degree of deuteration of compound A below, in Figure 3 In the MS plot, the molecular weight of the following starting material is set to 506, and the maximum molecular weight (median) of the following compound A is set to 527. It can then be determined that approximately 81% of the hydrogen has been deuterated, because 21 of the 26 hydrogens at the substituted positions in the following starting material have been replaced by deuterium.

[0181]

[0182] In this specification, D refers to deuterium.

[0183] According to one exemplary embodiment of this specification, chemical formula 1 is selected from any of the following compounds.

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208] According to one exemplary embodiment of the present specification, Chemical Formula 1 is any one selected from the following compounds.

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245] According to one exemplary embodiment of the present specification, Chemical Formula 1 is any one selected from the following compounds.

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288] The present specification provides an organic light emitting device including the compound.

[0289] In the present specification, when a member is "on" another member, this includes not only a case where the member is in contact with the other member, but also a case where a further member is present between the two members.

[0290] In the present specification, when a part "includes" a constituent element, unless otherwise specifically described, this does not mean excluding another constituent element but means that another constituent element can also be included.

[0291] In the present specification, a "layer" has the same meaning as "film" commonly used in the art, and means a coating layer covering a target area. The size of a "layer" is not limited, and the size of each "layer" can be the same as or different from each other. According to one exemplary embodiment, the size of a "layer" can be the same as the size of the entire device, can correspond to the size of a specific functional area, and can also be as small as a single sub-pixel.

[0292] In the present specification, when a specific A material is contained in a B layer, this means both of the following: i) the fact that one or more A materials are contained in one B layer; and ii) the fact that the B layer is composed of one or more layers and the A material is contained in one or more layers of the B layer of multiple layers.

[0293] In the present specification, when a specific A material is contained in a C layer or a D layer, this means all of the following: i) the fact that the A material is contained in one or more layers of the C layer having one or more layers; ii) the fact that the A material is contained in one or more layers of the D layer having one or more layers; and iii) the fact that the A material is contained in each of the C layer having one or more layers and the D layer having one or more layers.

[0294] The present specification provides an organic light emitting device, which includes: a first electrode; a second electrode disposed to face the first electrode; and an organic material layer having one or more layers disposed between the first electrode and the second electrode, wherein one or more layers of the organic material layer contain a compound represented by Chemical Formula 1.

[0295] The organic material layer of the organic light emitting device of the present specification can also have a single layer structure, but can have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic material layer can have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, etc. However, the structure of the organic light emitting device is not limited thereto, and can include a smaller number of organic layers.

[0296] According to one exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer contains the compound.

[0297] According to one exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer contains the compound as a host of the light emitting layer.

[0298] According to one exemplary embodiment of the present specification, the light emitting layer further contains one or more hosts different from the compound of Chemical Formula 1.

[0299] As the host different from the compound of Chemical Formula 1, any anthracene-based host used in the art can be used without limitation, and the host is not limited thereto.

[0300] According to one exemplary embodiment of the present specification, the light emitting layer contains a host and a dopant.

[0301] According to one exemplary embodiment of the present specification, the light emitting layer contains a host and a dopant, and the host contains the compound represented by Chemical Formula 1.

[0302] According to one exemplary embodiment of the present specification, the dopant is a blue dopant.

[0303] According to one exemplary embodiment of the present specification, the organic light emitting device is a blue organic light emitting device.

[0304] According to one exemplary embodiment of the present specification, the light emitting layer comprises two or more mixed hosts, and one or more of the two or more mixed hosts comprises the compound represented by Chemical Formula 1.

[0305] According to one exemplary embodiment of the present specification, the light emitting layer comprises two or more mixed hosts, at least one of the two or more mixed hosts comprises the compound represented by Chemical Formula 1, and the rest comprises an anthracene-based compound different from Chemical Formula 1.

[0306] An anthracene-based host used in the art can be used without limitation, as long as at least one of the two or more mixed hosts comprises the compound represented by Chemical Formula 1 and the rest is different from Chemical Formula 1, and the mixed host is not limited thereto.

[0307] According to one exemplary embodiment of the present specification, one or more of the mixed hosts must comprise a deuterium-substituted anthracene-based compound, the rest comprises a non-deuterium-substituted anthracene-based compound, and one of them comprises Chemical Formula 1.

[0308] According to one exemplary embodiment of the present specification, two or more of the mixed hosts must comprise a deuterium-substituted anthracene-based compound, and one of them comprises Chemical Formula 1.

[0309] The organic light emitting device using two or more mixed hosts according to one exemplary embodiment of the present specification aims to improve the performance of the device by combining the advantages of each host, and for example, when two hosts are mixed, one host having a high efficiency and low voltage effect and one host having a long service life effect can be mixed to manufacture an organic light emitting device having a high efficiency, low voltage, and long service life effect.

[0310] According to one exemplary embodiment of the present specification, the organic light emitting device has a maximum emission wavelength (λ 最大 ) in an emission spectrum of 400 nm to 470 nm.

[0311] According to one exemplary embodiment of the present specification, the light emitting layer comprises a host and a dopant, and the dopant is a fluorescent dopant.

[0312] According to one exemplary embodiment of the present specification, the light-emitting layer includes a host and a dopant, and the dopant includes one or more selected from a pyrene-based compound and a non-pyrene-based compound.

[0313] The pyrene-based compound and the non-pyrene-based compound can be used without limitation as long as it is a compound used in the art, and is not limited thereto.

[0314] According to one exemplary embodiment of the present specification, the non-pyrene-based compound includes a boron-based compound.

[0315] According to one exemplary embodiment of the present specification, the light-emitting layer includes a host and a dopant, the host includes a compound represented by Chemical Formula 1, and the dopant includes one or more selected from a pyrene-based compound and a non-pyrene-based compound.

[0316] According to one exemplary embodiment of the present specification, the light-emitting layer includes a host and a dopant in a weight ratio of 0.1:99.9 to 20:80.

[0317] According to one exemplary embodiment of the present specification, the light-emitting layer includes a host and a dopant in a weight ratio of 95:5 to 99:1.

[0318] In one exemplary embodiment of the present specification, the organic material layer includes the compound, and the compound has a band gap energy of 2.9 eV or more.

[0319] According to one exemplary embodiment of the present specification, the organic light-emitting device further includes one or two or more layers selected from a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer.

[0320] According to one exemplary embodiment of the present specification, the organic light-emitting device includes: a first electrode; a second electrode disposed to face the first electrode; a light-emitting layer disposed between the first electrode and the second electrode; and an organic material layer having two or more layers disposed between the light-emitting layer and the first electrode or between the light-emitting layer and the second electrode.

[0321] According to one exemplary embodiment of the present specification, as the organic material layer having two or more layers between the light-emitting layer and the first electrode or between the light-emitting layer and the second electrode, two or more can be selected from a light-emitting layer, a hole transport layer, a hole injection layer, a hole injection and transport layer, an electron blocking layer, a hole blocking layer, an electron injection layer, an electron transport layer, and an electron injection and transport layer.

[0322] According to one exemplary embodiment of the present specification, a hole transport layer having two or more layers is included between the light-emitting layer and the first electrode. The hole transport layer having two or more layers can contain materials that are the same as or different from each other.

[0323] According to one exemplary embodiment of the present specification, the first electrode is an anode or a cathode.

[0324] According to one exemplary embodiment of the present specification, the second electrode is a cathode or an anode.

[0325] According to one exemplary embodiment of the present specification, the organic light-emitting device can be a normal type organic light-emitting device in which an anode, an organic material layer having one or more layers, and a cathode are sequentially stacked on a substrate.

[0326] According to one exemplary embodiment of the present specification, the organic light-emitting device can be an inverted type organic light-emitting device in which a cathode, an organic material layer having one or more layers, and an anode are sequentially stacked on a substrate.

[0327] For example, the structure of the organic light-emitting device according to one exemplary embodiment of the present specification is exemplified in Figure 1 and Figure 2 . Figure 1 and Figure 2 The organic light-emitting device is exemplified, and the organic light-emitting device is not limited thereto.

[0328] Figure 1 The structure of the organic light-emitting device in which a first electrode 2, an organic material layer 4, and a second electrode 3 are sequentially stacked on a substrate 1 is exemplified. The compound is contained in the organic material layer.

[0329] Figure 2 The structure of the organic light-emitting device in which a first electrode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 8, a hole blocking layer 9, an electron injection and transport layer 10, and a second electrode 3 are sequentially stacked on a substrate 1 is exemplified. In this case, the compound is contained in the light-emitting layer 8.

[0330] The organic light-emitting device of the present specification can be manufactured by materials and methods known in the art, except that the light-emitting layer contains the compound, i.e., the compound represented by Chemical Formula 1.

[0331] When the organic light-emitting device includes a plurality of organic material layers, the organic material layers can be formed of the same material or different materials.

[0332] For example, the organic light emitting device of the present specification can be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. In this case, the organic light emitting device can be manufactured by depositing a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form an anode by using a physical vapor deposition (PVD) method such as sputtering or electron beam evaporation, forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer on the anode, and then depositing a material that can be used as a cathode on the organic material layer. In addition to the above-described method, the organic light emitting device can be manufactured by sequentially depositing a second electrode material, an organic material layer, and a first electrode material on a substrate.

[0333] Further, when the organic light emitting device is manufactured, the compound represented by Chemical Formula 1 can be formed into an organic material layer not only by a vacuum deposition method but also by a solution application method. Here, the solution application method means spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited thereto.

[0334] In addition to the above-described method, the organic light emitting device can be manufactured by sequentially depositing a second electrode material, an organic material layer, and a first electrode material on a substrate. However, the manufacturing method is not limited thereto.

[0335] As the first electrode material, a material having a high work function is generally preferred to facilitate hole injection into the organic material layer. Examples thereof include a metal such as vanadium, chromium, copper, zinc, and gold, or an alloy thereof; a metal oxide such as zinc oxide, indium oxide, indium tin (ITO) oxide, and indium zinc (IZO) oxide; a combination of a metal and an oxide such as ZnO:Al or SnO2:Sb; a conductive polymer such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline; and the like, but is not limited thereto.

[0336] As the second electrode material, a material having a low work function is generally preferred to facilitate electron injection into the organic material layer. Examples thereof include a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or an alloy thereof; a multi-layered structure material such as LiF / Al or LiO2 / Al; and the like, but is not limited thereto.

[0337] The light-emitting layer can include a host material and a dopant material. When an additional light-emitting layer is included in addition to the light-emitting layer including the compound of Chemical Formula 1 according to one exemplary embodiment of the present specification, examples of the host material include fused and / or non-fused aromatic ring derivatives, heterocycle-containing compounds, and the like. Specific examples of the fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and specific examples of the heterocycle-containing compounds include dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like, but examples are not limited thereto.

[0338] Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, the aromatic amine derivative is a fused aromatic ring derivative having a substituted or unsubstituted arylamine group, and examples thereof include pyrene, anthracene, chrysene, indenopyrene, and the like having an arylamine group, but are not limited thereto. In addition, the styrylamine compound is a compound in which a substituted or unsubstituted arylamine is substituted with at least one arylvinyl group, and one or two or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamine groups are substituted or unsubstituted. Specific examples thereof include styrylamine, styryldiamine, styryltriamine, styryltetramine, and the like, but are not limited thereto. In addition, examples of the metal complex include iridium complexes, platinum complexes, and the like, but are not limited thereto. Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, the aromatic amine derivative is a fused aromatic ring derivative having a substituted or unsubstituted arylamine group, and examples thereof include pyrene, anthracene, chrysene, indenopyrene, and the like having an arylamine group, but are not limited thereto. In addition, the styrylamine compound is a compound in which a substituted or unsubstituted arylamine is substituted with at least one arylvinyl group, and one or two or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamine groups are substituted or unsubstituted. Specific examples thereof include styrylamine, styryldiamine, styryltriamine, styryltetramine, and the like, but are not limited thereto. In addition, examples of the metal complex include iridium complexes, platinum complexes, and the like, but are not limited thereto.

[0339] According to one exemplary embodiment of the present specification, the dopant material includes a compound of the following Chemical Formula D-1 or D-2, but is not limited thereto.

[0340] [Chemical Formula D-1]

[0341]

[0342] In Chemical Formula D-1,

[0343] L101 and L102 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted arylene group, and

[0344] Ar101 to Ar104 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

[0345] [Chemical Formula D-2]

[0346]

[0347] In Chemical Formula D-2,

[0348] T1to T5are the same as or different from each other, and are each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine group; or a substituted or unsubstituted aryl group,

[0349] t3and t4are each an integer of 1 to 4,

[0350] t5is an integer of 1 to 3,

[0351] when t3is 2 or more, two or more T3are the same as or different from each other,

[0352] when t4is 2 or more, two or more T4are the same as or different from each other, and

[0353] when t5is 2 or more, two or more T5are the same as or different from each other.

[0354] According to one exemplary embodiment of the present specification, L101and L102are a direct bond.

[0355] According to one exemplary embodiment of the present specification, Ar101to Ar104are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

[0356] According to one exemplary embodiment of the present specification, Ar101to Ar104are the same as or different from each other, and are each independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

[0357] According to one exemplary embodiment of the present specification, Ar101to Ar104are the same as or different from each other, and are each independently a methyl-substituted phenyl group; or a dibenzofuranyl group.

[0358] According to one exemplary embodiment of the present specification, Chemical Formula D-1 is represented by the following compound.

[0359]

[0360] According to one exemplary embodiment of the present specification, T1to T5are the same as or different from each other, and are each independently hydrogen; a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl amine group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0361] According to one exemplary embodiment of the present specification, T1 to T5 are the same as or different from each other, and each is independently hydrogen; a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic arylamine group having 6 to 30 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, which is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms.

[0362] According to one exemplary embodiment of the present specification, T1 to T5 are the same as or different from each other, and each is independently hydrogen; a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic arylamine group having 6 to 30 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, which is unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms.

[0363] According to one exemplary embodiment of the present specification, Chemical Formula D-2 is represented by the following compound.

[0364]

[0365] The hole injection layer is a layer that receives holes from the electrode. It is preferable that the hole injection material has a capability of transporting holes, and has an effect of receiving holes from the anode and an excellent hole injection effect to the light-emitting layer or the light-emitting material. In addition, the hole injection material is preferably a material that is excellent in the capability of preventing excitons generated by the light-emitting layer from moving to the electron injection layer or the electron injection material. In addition, the hole injection material is preferably a material that is excellent in the capability of forming a thin film. In addition, the highest occupied molecular orbital (HOMO) of the hole injection material is preferably a value between the work function of the anode material and the HOMO of the adjacent organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, and arylamine-based organic materials; hexacyno hexaazatriphenylene-based organic materials; quinacridone-based organic materials; perylene-based organic materials; anthraquinone, polyaniline, and polythiophene-based conductive polymers; and the like, but are not limited thereto.

[0366] According to one exemplary embodiment of the present specification, the hole injection layer includes a compound represented by the following Chemical Formula HI-1, but is not limited thereto.

[0367] [Chemical Formula HI-1]

[0368]

[0369] In Chemical Formula HI-1,

[0370] at least one of X'1 to X'6 is N, and the rest are CH, and

[0371] R309 to R314 are the same as or different from each other and each is independently hydrogen; deuterium; cyano; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or are bonded to an adjacent group to form a substituted or unsubstituted ring.

[0372] According to one exemplary embodiment of the present specification, X'1 to X'6 are N.

[0373] According to one exemplary embodiment of the present specification, R309 to R314 are cyano.

[0374] According to one exemplary embodiment of the present specification, Chemical Formula HI-1 is represented by the following compound.

[0375]

[0376] The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer. The hole transport material is preferably a material having a high hole mobility that can receive holes from the anode or the hole injection layer and transfer the holes to the light-emitting layer. Specific examples thereof include an organic material based on arylamine, a conductive polymer, a block copolymer having both a conjugated portion and a non-conjugated portion, etc., but are not limited thereto.

[0377] The electron blocking layer is a layer that can improve the lifespan and efficiency of the device by preventing electrons injected from the electron injection layer from passing through the light-emitting layer and entering the hole injection layer. As the electron blocking layer, a well-known material can be used without limitation, and the electron blocking layer can be formed between the light-emitting layer and the hole injection layer, between the light-emitting layer and the hole transport layer, or between the light-emitting layer and a layer that simultaneously injects and transports holes.

[0378] According to one exemplary embodiment of the present specification, the hole transport layer or the hole blocking layer comprises a compound of the following Chemical Formula HT-1, but is not limited thereto.

[0379] [Chemical Formula HT-1]

[0380]

[0381] In Chemical Formula HT-1,

[0382] R315 to R317 are the same as or different from each other and each is independently any one selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and a combination thereof, or are bonded to an adjacent group to form a substituted or unsubstituted ring,

[0383] r315 is an integer of 1 to 5, and when r315 is 2 or more, two or more R315s are the same as or different from each other, and

[0384] r316 is an integer of 1 to 5, and when r316 is 2 or more, two or more R316s are the same as or different from each other.

[0385] According to one exemplary embodiment of the present specification, R317 is a substituted or unsubstituted aryl; a substituted or unsubstituted heteroaryl, or is bonded to an adjacent group to form an aryl- or alkyl-substituted aromatic hydrocarbon ring.

[0386] According to one exemplary embodiment of the present specification, R317 is any one selected from a substituted or unsubstituted carbazolyl; a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted fluorenyl; and a combination thereof.

[0387] According to one exemplary embodiment of the present specification, R315 and R316 are the same as or different from each other, and each is independently a substituted or unsubstituted aryl, or is bonded to an adjacent group to form an aryl- or alkyl-substituted aromatic hydrocarbon ring.

[0388] According to one exemplary embodiment of the present specification, R315 and R316 are the same as or different from each other, and each is independently a substituted or unsubstituted phenyl; a substituted or unsubstituted naphthyl; or a substituted or unsubstituted carbazolyl.

[0389] According to one exemplary embodiment of the present specification, Chemical Formula HT-1 is represented by any one of the following compounds.

[0390]

[0391] The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light-emitting layer. The electron transport material is preferably a material having a high electron mobility that can well receive electrons from the cathode and transport the electrons to the light-emitting layer. Specific examples thereof include an Al complex of 8-hydroxyquinoline; a complex including Alq3; an organic radical compound; a hydroxyflavone-metal complex, and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material as used according to the related art. In particular, a suitable cathode material is a typical material having a low work function, followed by an aluminum layer or a silver layer. Specific examples thereof include cesium, barium, calcium, ytterbium, and samarium, each followed by an aluminum layer or a silver layer.

[0392] In one exemplary embodiment of the present specification, the electron transport layer includes a compound of the following Chemical Formula ET-1 or ET-2.

[0393] [Chemical Formula ET-1]

[0394]

[0395] [Chemical Formula ET-2]

[0396]

[0397] In Chemical Formula ET-1 or ET-2,

[0398] R601to R604are the same as or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted alkyl; a substituted or unsubstituted aryl; or a substituted or unsubstituted heterocyclic group.

[0399] In one exemplary embodiment of the present specification, R601to R604are the same as or different from each other, and each independently a substituted or unsubstituted aryl; or a substituted or unsubstituted heterocyclic group.

[0400] In one exemplary embodiment of the present specification, R601to R604are the same as or different from each other, and each independently a substituted or unsubstituted aryl.

[0401] In one exemplary embodiment of the present specification, R601to R604are the same as or different from each other, and each independently a substituted or unsubstituted aryl having 6 to 30 carbon atoms.

[0402] In one exemplary embodiment of the present specification, R601to R604are the same as or different from each other, and each independently a substituted or unsubstituted aryl having 6 to 20 carbon atoms.

[0403] In one exemplary embodiment of the present specification, R601to R604are the same as or different from each other, and each independently a substituted or unsubstituted aryl having 6 to 10 carbon atoms.

[0404] In one exemplary embodiment of the present specification, R601to R604are phenyl.

[0405] In one exemplary embodiment of the present specification, the compound of Chemical Formula ET-1 is represented by the following compound.

[0406]

[0407] In one exemplary embodiment of the present specification, the compound of Chemical Formula ET-2 is represented by the following compound.

[0408]

[0409] The electron injection layer is a layer that receives electrons from the electrode. It is preferable that the electron injection material be excellent in the ability to transport electrons, and have an effect of receiving electrons from the second electrode and an excellent electron injection effect on the light-emitting layer or light-emitting material. Furthermore, the electron injection material is preferably a material that prevents excitons generated by the light-emitting layer from moving to the hole injection layer and is excellent in the ability to form a thin film. Specific examples thereof include fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidenemethane, anthrone, etc., and derivatives thereof; metal complex compounds; nitrogen-containing 5-membered ring derivatives; and the like, but are not limited thereto.

[0410] Examples of the metal complex compound include lithium 8-hydroxyquinolate, zinc bis(8-hydroxyquinolate), copper bis(8-hydroxyquinolate), manganese bis(8-hydroxyquinolate), aluminum tris(8-hydroxyquinolate), aluminum tris(2-methyl-8-hydroxyquinolate), gallium tris(8-hydroxyquinolate), beryllium bis(10-hydroxybenzo[h]quinolate), zinc bis(10-hydroxybenzo[h]quinolate), chlorogallium bis(2-methyl-8-quinolinate), gallium bis(2-methyl-8-quinolinate)(o-cresol), aluminum bis(2-methyl-8-quinolinate)(1-naphthol), gallium bis(2-methyl-8-quinolinate)(2-naphthol), etc., but are not limited thereto.

[0411] According to one exemplary embodiment of the present specification, the electron injection and transport layer is a layer that transports electrons to the light-emitting layer. For the electron injection and transport layer, the materials exemplified for the electron transport layer and the electron injection layer can be used, but the materials are not limited thereto.

[0412] According to one exemplary embodiment of the present specification, the electron injection and transport layer can further include a metal complex compound. The metal complex compound is as described above.

[0413] The hole blocking layer is a layer that blocks holes from reaching the cathode, and can generally be formed under the same conditions as those of the electron injection layer. Specific examples thereof include oxadiazole derivatives or triazole derivatives, phenanthroline derivatives, aluminum complexes, etc., but are not limited thereto.

[0414] According to one exemplary embodiment of the present specification, the hole blocking layer includes a compound of Chemical Formula EG-1 below, but is not limited thereto.

[0415] [Chemical Formula EG-1]

[0416]

[0417] In Chemical Formula EG-1,

[0418] ​at least one of G1to G18is -L5-Ar5, the others are hydrogen, or G1and G18are linked by -L51- to form a substituted or unsubstituted ring,

[0419] L5is a direct bond; or a substituted or unsubstituted arylene group,

[0420] Ar5is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0421] L51is O or S.

[0422] According to one exemplary embodiment of the present specification, L51is O.

[0423] According to one exemplary embodiment of the present specification, L51is S.

[0424] According to one exemplary embodiment of the present specification, G1and G18are linked by -L51- to form a substituted or unsubstituted heterocyclic ring.

[0425] According to one exemplary embodiment of the present specification, G1and G18are linked by -L51- to form a substituted or unsubstituted xanthene ring; or a substituted or unsubstituted thioxanthene ring.

[0426] According to one exemplary embodiment of the present specification, G1and G18are linked by -O- to form a substituted or unsubstituted xanthene ring.

[0427] According to one exemplary embodiment of the present specification, G1and G18are linked by -S- to form a substituted or unsubstituted thioxanthene ring.

[0428] According to one exemplary embodiment of the present specification, G1and G18are linked by -O- to form a xanthene ring.

[0429] According to one exemplary embodiment of the present specification, G1and G18are linked by -S- to form a thioxanthene ring.

[0430] According to one exemplary embodiment of the present specification, L5is a direct bond; or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0431] According to one exemplary embodiment of the present specification, L5is a direct bond; or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

[0432] According to one exemplary embodiment of the present specification, L5is a direct bond; or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0433] According to one exemplary embodiment of the present specification, L5is a direct bond; or a monocyclic or polycyclic arylene having 6 to 20 carbon atoms.

[0434] According to one exemplary embodiment of the present specification, L5is a direct bond; or a monocyclic or polycyclic arylene having 6 to 20 carbon atoms.

[0435] According to one exemplary embodiment of the present specification, Ar5is a substituted or unsubstituted triazinyl.

[0436] According to one exemplary embodiment of the present specification, Ar5is a triazinyl unsubstituted or substituted with a monocyclic or polycyclic aryl having 6 to 30 carbon atoms.

[0437] According to one exemplary embodiment of the present specification, Ar5is a triazinyl substituted with a phenyl.

[0438] According to one exemplary embodiment of the present specification, EG-1 is represented by the following compound.

[0439]

[0440] The organic light emitting device according to the present specification can be a top emission type, a bottom emission type, or a dual emission type, according to the materials used.

[0441] The organic light emitting device according to the present specification can be included and used in various electronic devices. For example, the electronic device can be a display panel, a touch panel, a solar module, a lighting device, etc., and is not limited thereto.

[0442] Inventive Embodiments

[0443] Hereinafter, the present specification will be described in detail by referring to examples, comparative examples, etc. for specifically describing the present specification. However, the examples and comparative examples according to the present specification can be modified in various forms, and should not be interpreted as limiting the scope of the present specification to the examples and comparative examples described below in detail. The examples and comparative examples of the present specification are provided to more completely explain the present specification to those of ordinary skill in the art.

[0444] <Preparation Example 1> Synthesis of Chemical Formula W

[0445] 1) Synthesis of Chemical Formula M

[0446]

[0447] After adding SM1 (1 equivalent) and SM2 (1.05 equivalents) to tetrahydrofuran (excess), 2M aqueous potassium carbonate solution (30 volume ratio compared to THF) was added thereto, and tetrakis triphenylphosphine palladium (2 mol%) was added thereto, and then the resulting mixture was heated and stirred for 10 hours. After the temperature was decreased to room temperature and the reaction was terminated, the aqueous potassium carbonate solution was removed to separate layers. After determining that the reaction was terminated, extraction was performed at room temperature to remove the solvent, potassium carbonate (1.5 equivalents) and dimethylformamide (excess) were added thereto, and the resulting mixture was heated and stirred under reflux for 5 hours. After determining that the reaction was terminated, water (1.5 volume ratio compared to the added dimethylformamide) was added thereto, and the precipitated solid was filtered. The solid was extracted with chloroform and water, and then purified by recrystallization using chloroform and ethanol to prepare Chemical Formula M (M1 to M3).

[0448] In the reaction scheme, R9and R 10 are the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted naphthyl, m is an integer of 1 to 4, and n is an integer of 1 to 3.

[0449] M1 to M3 in Table 1 were synthesized in the same manner as in the method of synthesizing Chemical Formula M, except that SM1 and SM2 were changed.

[0450] [Table 1]

[0451]

[0452] 2) Synthesis of Chemical Formula T

[0453]

[0454] SM3 (1 equivalent, Chemical Formula M synthesized above) was put into tetrachloroethane (excess), SM2 (10 equivalents, <pre-mixed solution (D2O:Tf2O = 4:1 ratio)) was added dropwise thereto, and then the resulting mixture was stirred at 140°C for 1 hour. After the mixture was cooled to room temperature, the mixture was extracted with saturated aqueous sodium bicarbonate solution to separate layers, and ethanol was added to filter the solidified compound. The foregoing process was repeated once, and recrystallization was performed with ethyl acetate and ethanol to prepare Chemical Formula T (T1 to T3).

[0455] In the reaction scheme, R9and R 10 are the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted naphthyl, m is an integer of 1 to 4, and n is an integer of 1 to 3.

[0456] T1 to T3 in Table 2 were synthesized in the same manner as in the method for synthesizing chemical formula T, except that SM3 was changed.

[0457] [Table 2]

[0458]

[0459] 3) Synthesis of chemical formula N

[0460]

[0461] After adding SM4 (1 equivalent, chemical formula M or T synthesized above) and SM5 (1.1 equivalent) to tetrahydrofuran (excess), 2M aqueous potassium carbonate solution (30 v / v to THF) was added, followed by the addition of tetra(triphenylphosphine)palladium (2 mol%). The resulting mixture was then heated and stirred at 85 °C for 10 hours. After lowering the temperature to room temperature and terminating the reaction, the layer was separated by removing the aqueous potassium carbonate solution, and the residue was recrystallized from the residue with ethyl acetate and ethanol to prepare chemical formulas N (N1 to N19).

[0462] In the reaction scheme, R9 and R 10 They may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted naphthyl, m being an integer from 1 to 4, n being an integer from 1 to 3, and Ar1 being an unsubstituted or deuterated phenyl; or an unsubstituted or substituted naphthyl with one or more of deuterium and alkyl.

[0463] N1 to N19 in Table 3 were synthesized in the same manner as in the method for synthesizing chemical formula N, except that SM4 and SM5 were changed.

[0464] [Table 3]

[0465]

[0466]

[0467]

[0468] 4) Synthesis of chemical formula W

[0469]

[0470] SM6 (1 equivalent, chemical formula N synthesized above) and SM7 (1.3 equivalent) were placed in 1,4-di In the alkane (12 times mass ratio compared to SM6), potassium acetate (3 equivalents) was added thereto, and the resulting mixture was stirred and refluxed. After stirring palladium acetate (0.02 equivalents) and tricyclohexylphosphine (0.04 equivalents) in 1,4-dioxane for 5 minutes, the resulting mixture was added thereto, and after 2 hours, the mixture was cooled to room temperature after determining termination of the reaction. After adding ethanol and water thereto, the resulting mixture was filtered and purified by recrystallization with ethyl acetate and ethanol to prepare Chemical Formula W (W1 to W19). In the alkane (12 times mass ratio compared to SM6), potassium acetate (3 equivalents) was added thereto, and the resulting mixture was stirred and refluxed. After stirring palladium acetate (0.02 equivalents) and tricyclohexylphosphine (0.04 equivalents) in 1,4-dioxane for 5 minutes, the resulting mixture was added thereto, and after 2 hours, the mixture was cooled to room temperature after determining termination of the reaction. After adding ethanol and water thereto, the resulting mixture was filtered and purified by recrystallization with ethyl acetate and ethanol to prepare Chemical Formula W (W1 to W19).

[0471] In the reaction scheme, R9and R 10 are the same as or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted alkyl; a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted naphthyl, m is an integer of 1 to 4, n is an integer of 1 to 3, and Ar1is a phenyl unsubstituted or substituted with deuterium; or a naphthyl unsubstituted or substituted with one or more of deuterium and alkyl.

[0472] W1 to W19 in Table 4 were synthesized in the same manner as in the method of synthesizing Chemical Formula W, except that SM6 and SM7 were changed.

[0473] [Table 4]

[0474]

[0475]

[0476]

[0477] <Preparation Example 2> Synthesis of Chemical Formula P1

[0478]

[0479] After adding SM8 (1 equivalent) and SM9 (1.1 equivalent) to tetrahydrofuran (excess), 2M aqueous potassium carbonate solution (30 volume ratio compared to THF) was added thereto, and tetrakis(triphenylphosphine)palladium (2 mol%) was added thereto, and then the resulting mixture was heated and stirred at 85°C for 10 hours. After lowering the temperature to room temperature and terminating the reaction, the layer was separated by removing the aqueous potassium carbonate solution, and the remaining was recrystallized with chloroform and ethyl acetate to prepare Chemical Formula A (A1 to A19).

[0480] In the reaction scheme, R9and R 10each independently of one another and each independently of the other, are hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted naphthyl, m is an integer from 1 to 4, n is an integer from 1 to 3, Ar1is unsubstituted or deuterium-substituted phenyl; or naphthyl which is unsubstituted or substituted by one or more of deuterium and alkyl, and R' is deuterium; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl.

[0481] A1 to A19 in Table 5 were synthesized in the same manner as in the method of synthesizing Chemical Formula A, except that SM8 and SM9 were changed.

[0482] [Table 5]

[0483]

[0484]

[0485]

[0486] 2) Synthesis of Chemical Formula B

[0487]

[0488] After dissolving SM10 (Chemical Formula A, 1 equivalent) in tetrahydrofuran (excess), the temperature was lowered to 0°C, the temperature was stabilized, then N-bromosuccinimide (1 equivalent) was dissolved in dimethylformamide (3.5 times compared to NBS), and the resulting solution was added dropwise thereto. Thereafter, the reactant was warmed to room temperature and stirred for 1 hour, and 1N HCl (excess) was added thereto to terminate the reaction. After completion of the reaction, the solvent was removed by separating the layers, then the remaining was recrystallized with chloroform and ethyl acetate to prepare Chemical Formula B (B1 to B19).

[0489] In the reaction scheme, R9and R 10 each independently of one another and each independently of the other, are hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted naphthyl, m is an integer from 1 to 4, n is an integer from 1 to 3, and Ar1is unsubstituted or deuterium-substituted phenyl; or naphthyl which is unsubstituted or substituted by one or more of deuterium and alkyl.

[0490] B1 to B19 in Table 6 were synthesized in the same manner as in the method of synthesizing Chemical Formula B, except that SM10 was changed.

[0491] [Table 6]

[0492]

[0493]

[0494]

[0495] 3) Synthesis of Formula P1

[0496]

[0497] After adding SM11 (Formula B, 1 equivalent) and SM12 (1.1 equivalent) to tetrahydrofuran (excess), 2M aqueous potassium carbonate solution (30 volume ratio compared to THF) was added thereto, and tetrakis triphenylphosphine palladium (2 mol%) was added thereto, and then the resulting mixture was heated and stirred at 85°C for 10 hours. After lowering the temperature to room temperature and terminating the reaction, the layer was separated by removing the aqueous potassium carbonate solution, and the remaining was recrystallized with chloroform and ethyl acetate to prepare the above Formula P1 (Compounds 1 to 36).

[0498] In the reaction scheme, R9and R 10 are the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted naphthyl, m is an integer of 1 to 4, n is an integer of 1 to 3, and Ar1is phenyl unsubstituted or substituted with deuterium; or naphthyl unsubstituted or substituted with one or more of deuterium and alkyl.

[0499] Compounds 1 to 36 in Table 7 were synthesized in the same manner as in the method of synthesizing Formula P1, except that SM11 and SM12 were changed.

[0500] [Table 7]

[0501]

[0502]

[0503]

[0504]

[0505]

[0506]

[0507] <Preparation Example 3> Synthesis of Formula P2

[0508]

[0509] The reactant (Chemical Formula C, 1 equivalent) and trifluoromethanesulfonic acid (catalyst) were put in C6D6 (10 to 50 times mass ratio compared to the reactant), and the resulting mixture was stirred at 70°C for 10 to 100 minutes. After completion of the reaction, D2O (excess) was added thereto, the resulting solution was stirred for 30 minutes, and then trimethylamine (excess) was added dropwise thereto. The reaction solution was transferred to a separatory funnel, and extraction was performed with water and chloroform. The extract was dried over MgSO4, and then recrystallized by heating with toluene to obtain the compounds 37 to 43 of Table 8 below.

[0510] In the reaction scheme, R9and R 10 are the same as or different from each other, and each independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted naphthyl, m is an integer of 1 to 4, n is an integer of 1 to 3, and Ar1is phenyl unsubstituted or substituted with deuterium; or naphthyl unsubstituted or substituted with one or more of deuterium and alkyl.

[0511] The compounds 37 to 43 in Table 4 below were synthesized in the same manner, except that the reactant (Chemical Formula C) was changed.

[0512] For the reactant (Chemical Formula C) in Table 8 below, the compounds 1, 7, 9, 13, 19, 29, and 35 synthesized in Preparation Example 2 were applied, respectively. The compounds 37 to 43 in Table 4 (AN-D8+Z compounds) are compounds subjected to the deuterium substitution method using benzene-D6 and TFA (trifluoromethanesulfonic acid) as mentioned above, and the number of deuterium atoms is D(8+z) as a result of additional deuterium substitution to the compounds (AN-D8 compounds) in which only the hydrogens of anthracene in the entire skeleton are replaced with deuterium among the products in Table 4. z means the number of additional deuterium atoms randomly (preferably, in the order of reactivity) substituted at position 9 (dibenzofuran unit) and position 10 (biphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, terphenyl, etc.) of anthracene.

[0513] The compounds 37 to 43 in Table 8 below are compounds in which the dibenzofuran substituted at position 9 of anthracene and the aryl unit (biphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, terphenyl) substituted at position 10 are randomly substituted with additional deuterium after the compounds 1, 7, 13, 19, 29, and 35 in which only eight hydrogen atoms of anthracene are replaced with deuterium are synthesized. These are synthesized to understand the electrical properties and performance in a blue organic light-emitting device compared to the compounds in which only eight hydrogen atoms of anthracene are replaced with deuterium.

[0514] Compounds 37 to 43 in Table 8 below were prepared under the same reaction conditions, but had different substitution rates due to differences in steric hindrance of the reactant substituents, as shown in the following examples.

[0515] Example 1: Deuterium substitution rate of compound 1 -> compound 37: 29% -> 82%

[0516] Example 2: Deuterium substitution rate of compound 7 to compound 38: 27% -> 63%

[0517] Example 3: Deuterium substitution rate of compound 35 to compound 43: 25% -> 66%

[0518] [Table 8]

[0519]

[0520]

[0521] <Example 1> Manufacturing of OLEDs

[0522] As the positive electrode, a layer with a thickness of [thickness missing] is deposited on it. The ITO / Ag / ITO substrate was cut into 50mm × 50mm × 0.5mm pieces, placed in distilled water containing a dispersant, and ultrasonically washed. A product manufactured by Fischer Co. was used as the cleaning agent, and distilled water filtered twice using a filter manufactured by Millipore Co. was used as the distilled water. After washing the ITO for 30 minutes, ultrasonic washing was repeated twice for 10 minutes each time with distilled water. After washing with distilled water, ultrasonic washing was performed sequentially with isopropanol, acetone, and methanol solvents, followed by drying.

[0523] HI-1 is thermally vacuum deposited onto the prepared positive electrode to a thickness of [thickness missing]. This forms a hole injection layer, and a material of thickness HT1 for transporting holes is vacuum deposited on the hole injection layer to a thickness of [thickness value missing]. This forms a hole transport layer. Next, an electron blocking layer is formed using EB1. Then, the host compound 1 and dopant BD1 (2 wt%) synthesized in the vacuum deposition preparation example were deposited to a thickness of [missing information]. This forms a light-emitting layer. Subsequently, ET1 is deposited to a thickness of [thickness missing]. This forms a hole-blocking layer, and compounds ET2 and Liq are mixed in a 7:3 ratio to form a layer with a thickness of [missing information]. An electron transport layer was then deposited. Subsequently, magnesium and lithium fluoride (LiF) were deposited to a thickness of [thickness missing]. After forming a film as an electron injection layer, magnesium and silver (1:4) are used to form a film with a thickness of [missing information]. a negative electrode, and then depositing CP1 to a thickness of thereby completing the device. In the foregoing steps, the deposition rate of the organic material was maintained at 0.1 A each.

[0524]

[0525] Examples 2 to 43

[0526] As shown in Table 9 below, the organic light emitting devices of Examples 2 to 43 were manufactured by preparing in the same manner as in Example 1, except that Compounds 1 to 36 synthesized in Preparation Example 2 were used as the host material of the light emitting layer and BD1 or BD2 was used as the dopant material of the light emitting layer, respectively.

[0527] Examples a to d

[0528] As shown in Table 9 below, the organic light emitting devices of Examples a to d were manufactured by preparing in the same manner as in Example 1, except that the following compounds a to d synthesized as in Preparation Example 1 were used as the host material of the light emitting layer and BD1 was used as the dopant material of the light emitting layer, respectively.

[0529] Examples 44 to 57

[0530] As shown in Table 11 below, the organic light emitting devices of Examples 44 to 57 were manufactured by preparing in the same manner as in Example 1, except that Compounds 37 to 43 synthesized in Preparation Example 3 were used as the host material of the light emitting layer and BD1 or BD2 was used as the dopant material of the light emitting layer, respectively.

[0531] Comparative Examples 1-1 to 1-9 and Comparative Examples 2-1 to 2-9

[0532] As shown in Table 9 below, the organic light emitting devices of Comparative Examples 1-1 to 1-9 and Comparative Examples 2-1 to 2-9 were manufactured by preparing in the same manner as in Example 1, except that the following compounds were used as the host material of the light emitting layer and BD1 or BD2 was used as the dopant material of the light emitting layer, respectively.

[0533] Comparative Examples 3-1 to 3-43

[0534] As shown in Table 10 below, the organic light emitting devices of Comparative Examples 3-1 to 3-43 were manufactured by preparing in the same manner as in Example 1, except that the compounds in which all positions to be replaced with hydrogen in the compound skeleton of Compounds 1 to 43 were replaced with hydrogen were used as the host material of the light emitting layer and BD1 or BD2 was used as the dopant material of the light emitting layer, respectively.

[0535]

[0536]

[0537] Experimental Example

[0538] When an application of 20 mA / cm² is applied to the organic light-emitting devices manufactured in Examples 1 to 43, Comparative Examples 1-1 to 1-9, and Comparative Examples 2-1 to 2-9, 2 At the given current, voltage, efficiency, color coordinates, lifetime, deuterium substitution rate, and lifetime increase rate A (%) were measured, and the results are shown in Table 9 below. T95 refers to the time taken for the brightness to decrease to 95% of the initial brightness (1600 nits). The lifetime increase rate A (%) is the lifetime increase rate of Examples 1 to 43 compared to compound H (where all hydrogen atoms in the compound skeleton are hydrogen atoms).

[0539] [Table 9]

[0540]

[0541]

[0542]

[0543]

[0544]

[0545]

[0546] As shown in Table 9 above, the organic light-emitting devices of Examples 1 to 43 using the compound represented by Chemical Formula 1 of the present invention exhibit better characteristics in terms of driving voltage, efficiency, and lifespan compared to the organic light-emitting devices of Comparative Examples 1-1 to 1-9 and Comparative Examples 2-1 to 2-9.

[0547] Specifically, Examples 1 to 43 comprise compounds in which all anthracene in Formula 1 is deuterated and position 10 of anthracene is substituted with biphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, or triphenyl.

[0548] Comparative Examples 1-1 to 1-9 comprise compounds in which anthracene is unsubstituted with deuterium and position 10 of anthracene is substituted with a phenyl group, and Comparative Examples 2-1 to 2-9 comprise compounds in which all anthracene is substituted with deuterium and position 10 of anthracene is substituted with a phenyl group.

[0549] It can be seen that, compared to Comparative Examples 1-1 to 1-9 in which anthracene is not substituted with deuterium, the organic light emitting device including the compound in which all of anthracene is substituted with deuterium and position 10 of anthracene is substituted with a biphenyl group, a naphthyl group, a phenyl naphthyl group, a naphthyl phenyl group, or a terphenyl group according to one exemplary embodiment of the present specification results in an increase in binding energy by deuterium substitution, and thus is excellent in stability and lifespan of a blue device.

[0550] Further, it can be seen that, compared to Comparative Examples 2-1 to 2-9 in which all of anthracene is substituted with deuterium and position 10 of anthracene is substituted with a phenyl group, when a naphthyl group and an additional aryl group are introduced, the total hole mobility tends to increase, and the efficiency increases, and the device is excellent in stability and lifespan.

[0551] It can be determined that, compared to Comparative Examples 1-1 to 1-9, Examples a to d including the compound in which all of anthracene is substituted with deuterium and two phenyl groups are substituted at the 3,3' end of dibenzofuran are excellent in voltage, efficiency, and lifespan, but similarly have low voltage characteristics compared to Examples 4, 15, 21, and 24 including the compound in which one phenyl group is substituted at the 3 end of dibenzofuran, but are slightly inferior in efficiency.

[0552] As previously mentioned, the lifespan increase rate A (%) of Examples 1 to 43 is a lifespan increase rate compared to an H compound (a compound in which all of the hydrogen atoms in the compound skeleton are hydrogen atoms), and is determined by referring to the device results of the H compound of each compound in Comparative Examples 3-1 to 3-43 in Table 10 below.

[0553] [Table 10]

[0554]

[0555]

[0556]

[0557]

[0558] When a current of 20 mA / cm2was applied to the organic light emitting device manufactured in Examples 44 to 57, the voltage, efficiency, color coordinates, lifespan, deuterium exchange rate, and lifespan increase rate were measured, and the results are shown in Table 11 below. T95 means the time taken for the luminance to decrease to 95% of the initial luminance (1600 nits). 2

[0559] ​The use-life increase rate B (%) is the use-life increase rate of Examples 44 to 57 compared to the H compound (a compound in which all hydrogen atoms in the compound skeleton are hydrogen atoms), and the use-life increase rate C (%) is the use-life increase rate of Examples 44 to 57 compared to the AN-D8 compound (a compound in which only the hydrogens in anthracene are replaced with deuterium).

[0560] [Table 11]

[0561]

[0562]

[0563] For detailed analysis, Table 12 below is described.

[0564] [Table 12]

[0565]

[0566]

[0567] Examples 44 to 57 described in Table 11 and Table 12 are organic light emitting devices including compounds 37 to 43 (compounds in which compounds 1, 7, 9, 13, 19, 29, and 35 (compounds in which only eight hydrogen atoms in anthracene are replaced with deuterium) are subjected to additional deuterium substitution by Preparation Example 3). It can be determined that the increase in the deuterium substitution rate in Examples 44 to 57 does not result in a significant increase (7% to 12%) in the use-life of the device. It can thus be determined that additional deuterium substitution other than the anthracene skeleton results in an increase in the use-life, but the introduction of deuterium into the anthracene skeleton results in a major effect of increasing the use-life.

[0568] From the above results, it can be determined that the use of the compound according to the present application can adjust the effect of smoothly injecting holes into the light emitting layer, and depending on the chemical structure, excellent characteristics in efficiency, driving voltage, and use-life are exhibited from the balance of holes and electrons.

Claims

1. A compound represented by the following Chemical Formula 1: [Chemical Formula 1] wherein In Chemical Formula 1, R1 to R8 are the same as or different from each other, and each is independently deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, R9and R 10 R9and R each independently, hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; or substituted or unsubstituted naphthyl, m is an integer of 1 to 4, n is an integer of 1 to 3, Ar1 is phenyl unsubstituted or substituted with deuterium; or naphthyl unsubstituted or substituted with one or more of deuterium and alkyl, and Ar2 is biphenyl unsubstituted or substituted with deuterium or alkyl; terphenyl unsubstituted or substituted with deuterium or alkyl; naphthyl unsubstituted or substituted with deuterium or alkyl; phenylnaphthyl unsubstituted or substituted with deuterium or alkyl; or naphthylphenyl unsubstituted or substituted with deuterium or alkyl. 2.The compound according to claim 1, wherein Ar2 of Chemical Formula 1 is any one of the following Chemical Formulas Ar2-1 to Ar2-8: In Chemical Formulas Ar2-1 to Ar2-8, R', R'', and R''' are the same as or different from each other, and each is independently hydrogen; deuterium; or a substituted or unsubstituted alkyl group, x1 is an integer of 1 to 3, x2 is an integer of 1 to 4, x3 is an integer of 1 to 6, x4 is an integer of 1 to 7, y1 is an integer of 1 to 4, y2 is an integer of 1 to 5, y3 is an integer of 1 to 7, and z1 is an integer of 1 to 5, and means the parts to be connected. 3.The compound according to claim 1, wherein Chemical Formula 1 is any one of the following Chemical Formulas 1-1 to 1-3: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] In Chemical Formulas 1-1 to 1-3, R1to R 10 m, n, and Ar2are defined in the same manner as in Chemical Formula 1, and R 11 to R 17 R and R are the same or different from each other and each independently hydrogen or deuterium. 4.The compound according to claim 1, wherein Chemical Formula 1 is any one of the following Chemical Formulas 2-1 to 2-3: [Chemical Formula 2-1] [Chemical Formula 2-2] [Chemical Formula 2-3] In Chemical Formulas 2-1 to 2-3, R1to R 10 m, n, and Ar2are the same as defined in Chemical Formula 1, and R 11 to R 15 are the same or different from each other and are each independently hydrogen or deuterium. 5.The compound according to claim 1, wherein Chemical Formula 1 is any one of the following Chemical Formulas 2-4 to 2-6: [Chemical Formula 2-4] [Chemical Formula 2-5] [Chemical Formula 2-6] In Chemical Formulas 2-4 to 2-6, R1to R 10 m, n, and Ar2are defined in the same manner as in Chemical Formula 1, and R 11 to R 17 R and R are the same or different from each other and each independently hydrogen or deuterium. 6.The compound according to claim 1, wherein Chemical Formula 1 is any one of the following Chemical Formulas 2-7 to 2-9: [Chemical Formula 2-7] [Chemical Formula 2-8] [Chemical Formula 2-9] In Chemical Formulas 2-7 to 2-9, R1to R 10 m, n, and Ar2are defined in the same manner as in Chemical Formula 1, and R 11 to R 17 R and R are the same or different from each other and each independently hydrogen or deuterium. 7.The compound according to claim 1, wherein Chemical Formula 1 is any one of the following Chemical Formulas 3-1 to 3-12: In Chemical Formulas 3-1 to 3-12, R1to R 10 The definitions of m and n are the same as in Chemical Formula 1. R 11 to R 17 are identical or different from each other and are each independently hydrogen or deuterium, R' is hydrogen; deuterium; or an alkyl group, and x3 is an integer of 1 to 6, and x4 is an integer of 1 to 7. 8.The compound according to claim 1, wherein Chemical Formula 1 is any one of the following Chemical Formulas 4-1 to 4-12: In Chemical Formulas 4-1 to 4-12, R1to R 10 m and n are the same as defined in Chemical Formula 1, R 11 to R 17 are identical or different from each other and are each independently hydrogen or deuterium, R', R'', and R''' are the same as or different from each other, and each is independently hydrogen; deuterium; or an alkyl group, and x1 is an integer of 1 to 3, x2 is an integer of 1 to 4, y1 is an integer of 1 to 4, y2 is an integer of 1 to 5, y3 is an integer of 1 to 7, and z1 is an integer of 1 to 5.

9. The compound according to claim 1, wherein R1 to R8 of Formula 1 are all deuterium.

10. The compound according to claim 1, wherein R9 and R 10 are all deuterium.

11. The compound according to claim 1, wherein Ar1 of Formula 1 is phenyl all of which is substituted with deuterium; or naphthyl all of which is substituted with deuterium.

12. The compound according to claim 2, wherein R', R", and R'" of Formulae Ar2-1 to Ar2-8 are all deuterium.

13. The compound of claim 3, wherein R of Formula 1-1 to 1-3 11 to R 17 are all deuterium.

14. The compound according to claim 1, wherein the deuterium substitution rate of Formula 1 is 10% or more.

15. The compound according to claim 1, wherein the deuterium substitution rate of Formula 1 is 30% or more.

16. The compound according to claim 1, wherein the deuterium substitution rate of Formula 1 is 40% or more.

17. The compound according to claim 1, wherein Formula 1 is any one selected from the following compounds:

18.

19.

20. An organic light-emitting device comprising: a first electrode; a second electrode; and an organic material layer having one or more layers disposed between the first electrode and the second electrode, wherein one or more layers of the organic material layer comprises the compound according to any one of claims 1 to 19.

21. The organic light-emitting device according to claim 20, wherein the organic material layer comprises an emission layer, and the emission layer comprises the compound as a host of the emission layer.

22. The organic light-emitting device according to claim 21, wherein the emission layer further comprises a dopant.

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