© TXPMTKEA
`
`KR20210092513A
`
`KR20210092513A 20210726
`
`EPO
`
`SUBJECT OF THE INVENTION
`Organic electroluminescent device {ORGANIC ELECTROLUMINESCENT DEVICE}
`
`[0001]
`
`The present specification relates to an organic electroluminescent device.
`
`[0002]
`
`[0003]
`
`The organic electroluminescent device has a structure in which an organic thin film is disposed
`between two electrodes. Whena voltage is applied to the organic electroluminescent device
`having such a structure, electrons and holes injected from the two electrodes combine in the
`organic thin film to form a pair, and then disappear and emit light. The organic thin film may be
`composed of a single layer or multiple layers, if necessary.
`
`As materials used in organic electroluminescent devices, pure organic materials or complex
`compoundsin which an organic material and a metal are complexed account for most, and
`depending on the use, a hole injection material, a hole transport material, a light emitting material,
`an electron transport material, an electron injection material can be classified as Here, as the hole
`injection material or the hole transport material, an organic material having a p-type property, that
`is, an organic material that is easily oxidized and has an electrochemically stable state during
`oxidation, is mainly used. On the other hand, as an electron injection material or an electron
`transport material, an organic material having an n-type property, that is, an organic material that
`
`is easily reduced and has an electrochemically stable state during reduction is mainly used. As the
`light emitting layer material, a material having both p-type properties and n-type properties, thatis,
`a material having a stable form in both oxidation and reduction states is preferable, and excitons
`generated by recombination of holes and electrons in the light emitting layer are formed A material
`with high luminous efficiency that convertsit into light when it is formed is preferable.
`
`[0004]
`
`In order to improve the performance, lifespan or efficiency of an organic electroluminescent device,
`the developmentof a material for an organic thin film is continuously required.
`
`[0006]
`
`The present specification provides an organic electroluminescent device.
`
`[0007]
`
`One embodiment of the present specification is a cathode; anode; and a light emitting layer
`provided between the cathode and the anode, wherein the light emitting layer includes two types
`of hosts and one type of dopant represented by the following Chemical Formula 1, at least one of
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`the hosts is deuterium It provides an organic electroluminescent device having a substitution rate
`of 10% to 100%.
`
`KR20210092513A
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`[0008]
`
`[Formula 1]
`
`[0009]
`
`[image]
`
`[0010]
`
`In Formula 1,
`
`[0011]
`
`At least one of R1 to R10 is Formula 2,
`
`[0012]
`
`[Formula 2]
`
`[0013]
`
`[image]
`
`[0014]
`
`Of R1 to R10, the groups not bonded to Formula 2 are each independently hydrogen, deuterium,
`a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 5 to C
`50 aryl group, or a substituted or unsubstituted C C group. From the group consisting of a 3 to
`30 cycloalkyl group, a substituted or unsubstituted C1 to C30 alkylsilyl group, a substituted or
`unsubstituted C5 to C30 arylsilyl group, a cyano group, a nitro group, a hydroxyl group anda
`halogen group. selected,
`
`[0015]
`
`*in Formula 2 represents a connection site with at least one of R1 to R10,
`
`[0016]
`
`L1 is a direct bond, or a substituted or unsubstituted arylene group having 5 to 50 carbon atoms,
`
`[0017]
`
`p is an integer from 1 to 5,
`
`[0018]
`
`Ar is a substituted or unsubstituted aryl group having 5 to 30 carbon atoms.
`
`[0019]
`
`The organic electroluminescent device according to the embodiments described herein may
`improve device efficiency, driving voltage characteristics, or lifespan characteristics by mixing and
`using the specific host material described above.
`
`[0020]
`
`1 and 3 show an organic electroluminescent device according to an embodiment of the present
`specification. 2 is a TLC-MS graph for calculating the deuterium substitution rate.
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`KR20210092513A
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`[0021]
`
`Hereinafter, the present specification will be described in detail.
`
`[0022]
`
`An organic electroluminescent device according to an exemplary embodiment of the present
`specification includes a cathode; anode; and a light emitting layer provided between the cathode
`and the anode, wherein the light emitting layer includes two types of hosts and one type of dopant
`represented by Chemical Formula 1, and at least one of the hosts is deuterium It is characterized
`in that the substitution rate is 10%to 100%.
`
`[0023]
`
`The embodiment is characterized in that the light emitting layer of the organic electroluminescent
`device includes two kinds of anthracene-based hosts, and at least one kind of host is deuterated.
`
`Thereby, it is possible to obtain an organic electroluminescent device with significantly improved
`lifespan while maintaining excellent efficiency.
`
`[0024]
`
`Specifically, anthracene derivatives containing an aryl-based substituent have stable performance
`when usedas a host of an organic electroluminescent device and are being commercialized to
`date. However, since a single host has opposite effects of lifetime and efficiency, it wasdifficult
`to satisfy both. As an alternative, a mixed host has been used, but it is difficult to improve the
`performanceof the fabricated color device becauseit cannot deviate from the range of basic
`performance of organic compounds.
`
`[0025]
`
`Accordingly, deuteration of the anthracene-based host is being sought as a way to maintain the
`lifespan while maximizing the efficiency of the light emitting layer. While maintaining the efficiency
`of the light emitting device, the lifespan problem was greatly improved. The carbon-deuterium
`bond is stronger than the carbon-hydrogen bond. Since deuterium has a higher mass value than
`hydrogen, the energy of bonding is increased by lowering the zero point energy with carbon.
`
`[0026]
`
`Zero point energy =
`[image]
`
`[0027]
`
`The light emitting layer of the organic electroluminescent device is a region having a direct effect
`of emitting light, a section in which a loss of molecules due to energy is large, and the molecule
`has many carbon-hydrogen bonds. By replacing a carbon-hydrogen bond of a certain ratio or more
`with a carbon-deuterium bond, the binding energy of the molecule can be increased, and thus the
`lifespan of the organic electroluminescent device can be improved.
`
`[0028]
`
`In the present specification, when a part "includes" a certain component, this means that other
`components maybe further included rather than excluding other components unless otherwise
`stated.
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`KR20210092513A
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`[0029]
`
`As used herein, the deuterium substitution ratio refers to a substitution ratio of deuterium in a
`molecule, and the following two methods arefollowed to determine the substitution distribution of
`deuterium in a molecule. Among the following two methods, TLC-MS is a method for controlling the
`substitution ratio of deuterium in the process of synthesizing a compound.
`
`[0030]
`
`1. TLC-MS (Thin-Layer Chromatography/Mass Spectrometry) is used (synthesis process
`confirmation method)
`
`[0031]
`
`The substitution rate can be calculated based on the maximum value (max. value) of the
`distribution of molecular weights at the end of the reaction.
`
`[0032]
`
`For example, in the case of the compound shownin FIG. 2, 527 is viewed as the median value in
`the MS graph, and since a total of 21 Hs are substituted with D,
`it can be calculated as 21/26 * 100
`= 81%.
`
`[0033]
`
`2. Quantitative analysis using NMR
`
`[0034]
`
`
`integral amount of_total peak using the integration ratioon 1H NMR.
`
`DMF is added as an internal standard, and the D substitution rate can be calculated from the
`
`[0035]
`
`Examples of substituents in the present specification are described below, but are not limited
`thereto.
`
`[0036]
`
`The term "substitution" means that a hydrogen atom bondedto a carbon atom of a compound
`
`is replaced with another substituent, and the position to be substituted is not limited as long as
`
`the position at which the hydrogen atom is substituted, that is, a position where the substituent is
`substitutable, is not limited, and when two or more are substituted , two or more substituents may
`be the same asor different from each other.
`
`[0037]
`
`Page 4
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`As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group;
`nitrile group; nitro group; imid; amide group; carbonyl group; ester group; hydroxyl group; a
`substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a
`substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; A
`substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthioxy group;
`a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy
`group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a
`substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted
`or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a
`substituted or unsubstituted aryl group; And it means thatit is substituted with one or two or more
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`KR20210092513A
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`substituents selected from the group consisting of a substituted or unsubstituted heterocyclic
`group, is substituted with a substituent to which two or more of the above-exemplified substituents
`are connected, or does not have any substituents. For example, "a substituent to which two or
`more substituents are connected" includes a heteroaryl group substituted with an aryl group; Or it
`may be an aryl group substituted with a heteroaryl group. That is, the biphenyl group may be an
`aryl group, and maybeinterpreted as a substituent in which two phenyl groups are connected.
`
`[0038]
`
`In the present specification, the halogen group maybefluorine, chlorine, bromine or iodine.
`
`[0039]
`
`In the present specification, the alkyl group may belinear or branched, and the numberof carbon
`atoms is not particularly limited, but is preferably 1 to 30. Specific examples include methyl,
`ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-
`ethyl-butyl, pentyl, n-pentyl , isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-
`methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethyloutyl, heptyl, n -Heptyl, 1-methylhexyl,
`
`cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl,
`2-propylpentyl, n-nonyl, 2,2-dimethyl heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-
`methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like.
`
`[0040]
`
`[0041]
`
`[0042]
`
`Page 5
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`In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to
`30 carbon atoms, and specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-
`dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl,
`3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc., but are limited thereto
`it is not
`
`In the present specification, the alkoxy group may bea straight chain, branched chain or cyclic
`chain. Although carbon number of an alkoxy group is not specifically limited, It is preferable that
`it is C1-C30. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-
`butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n -hexyloxy, 3,3-dimethylbutyloxy, 2-
`ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. may beIt is
`notlimited.
`
`In the present specification, the amine group is -NH2; an alkylamine group; N-alkylarylamine
`group; arylamine group; N-aryl heteroarylamine group; It may be selected from the group
`consisting of an N-alkylheteroarylamine group and a heteroarylamine group, and the number
`of carbon atoms is not particularly limited, but is preferably 0 to 30. Specific examples of the
`amine group include a methylamine group, a dimethylamine group, an ethylamine group, a
`diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group,
`an anthracenylamine group, and a 9-methyl-anthracenylamine group. , diphenylamine group,
`N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine
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`group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, N-bi Phenylnaphthylamine
`group, N-naphthylfluorenylamine group, N-phenylphenanthrenylamine group, N-
`biphenylphenanthrenylamine group, N-phenylfluorenylamine group, N-phenylterohenylamine group
`group, N-phenanthrenylfluorenylamine group, N-biphenylfluorenylamine group, and the like, but is
`not limited thereto.
`
`KR20210092513A
`
`[0043]
`
`In the present specification, the N-alkylarylamine group refers to an amine group in which an alkyl
`group and an aryl group are substituted with N of the amine group.
`
`[0044]
`
`In the present specification, the N-arylheteroarylamine group refers to an amine group in which an
`aryl group and a heteroaryl group are substituted with N of the amine group.
`
`[0045]
`
`In the present specification, the N-alkylheteroarylamine group refers to an amine group in which an
`alkyl group and a heteroaryl group are substituted with N of the amine group.
`
`[0046]
`
`In the present specification, the alkyl group in the alkylamine group, N-arylalkylamine group,
`alkylthioxy group, alkylsulfoxy group, and N-alkylheteroarylamine group is the same as the above-
`described alkyl group.
`
`[0047]
`
`The numberof carbon atoms of the acyl thiooxy group is not particularly limited, but is preferably
`1 to 30. Specific examples include a methylthioxy group, an ethylthioxy group, a tert-butylthioxy
`group, a hexylthioxy group, an octylthiooxy group, and the like, and the alkylsulfoxy group includes
`a mesyl, an ethylsulfoxy group, a propylsulfoxy group, a butylsulfoxy group, and the like, The
`presentinvention is not limited thereto.
`
`[0048]
`
`In the present specification, the alkenyl group may belinear or branched, and the numberof
`carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples include vinyl,
`1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-
`methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl,
`
`2-phenyl-2-( naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stiloenyl group, styrenyl group,
`
`and the like, but is not limited thereto.
`
`[0049]
`
`In the present specification, the alkynyl group maybelinear or branched, and the number of
`carbon atoms is not particularly limited, but is preferably 2 to 20. Specific examples include ethynyl,
`propynyl, butynyl, pentynyl, hexynyl, heptynyl, octynyl, nonynyl and the like, but is not limited
`thereto.
`
`[0050]
`
`In the present specification, the silyl group may be an alkylsilyl group or an arylsilyl group, and
`further may bea trialkylsilyl group or a triarylsilyl group. The number of carbon atoms ofthe silyl
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`KR20210092513A
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`group is not particularly limited, but preferably 1 to 30, the alkylsilyl group may have 1 to 30 carbon
`atoms, and the arylsilyl group may have 5 to 30 carbon atoms. Specifically, there are trimethylsilyl
`group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsily!
`group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc., but is not limited thereto. .
`
`[0051]
`
`In the present specification, the boron group may be -BR100R101, wherein R100 and R101 are
`the same or different, and each independently hydrogen; heavy hydrogen; halogen; nitrile group;
`a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon
`atoms; a substituted or unsubstituted C1-C30 linear or branched alkyl group; a substituted or
`unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And it may be
`selected from the group consisting of a substituted or unsubstituted monocyclic or polycyclic
`heteroaryl group having 2 to 30 carbon atoms.
`
`[0052]
`
`In the present specification, the phosphine oxide group specifically includes a diphenylphosphine
`oxide group, a dinaphthyl phosphine oxide group, and the like, but is not limited thereto.
`
`[0053]
`
`In the present specification, the aryl group is not particularly limited, but preferably has 6 to 30
`carbon atoms, and the aryl group may be monocyclic or polycyclic.
`
`[0054]
`
`Whenthe aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly
`limited, but preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may be a
`phenyl group, a biphenyl group, a terphenyl group, and the like, but is not limited thereto.
`
`[0055]
`
`Whenthe aryl group is a polycyclic aryl group, the numberof carbon atoms is not particularly
`limited. It is preferable that it is C10-30. Specifically, the polycyclic aryl group may be a naphthyl
`group, an anthracenyl group, a phenanthryl group, a triphenyl group, a pyrenyl group, a phenaleny!|
`group, a perylenyl group, a chrysenyl group, a fluorenyl group, a fluoranthenyl group, etc. , but is
`not limited thereto.
`
`[0056]
`
`In the present specification, the fluorenyl group may be substituted, and adjacent groups may
`combine with each other to form a ring.
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`

`[0057]
`
`Whenthe fluorenyl group is substituted, it may be
`[image]
`
`KR20210092513A
`
`[image]
`
`[image]
`
`[image]
`
`[image]
`and
`
`[image]
`. However, the present invention is not limited thereto.
`
`[0058]
`
`In the present specification, the aryl group in the aryloxy group, the arylthioxy group, the arylsulfoxy
`group, the N-arylalkylamine group, the N-arylheteroarylamine group and the arylphosphine group
`is the same as the above-described aryl group.
`
`[0059]
`
`The numberof carbon atoms of the aryloxy group is not particularly limited, but is preferably 6 to
`30. Specific examples include a phenoxy group, p-tolyloxy group, m-tolyloxy group, 3,5-dimethyl-
`phenoxy group, 2,4,6-trimethylohenoxy group, p-tert-butylphenoxy group, 3-biphenylox Group,
`4-biphenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-methyl-1-naphthyloxy group,
`5-methyl-2-naphthyloxy group, 1-anthryloxy group, 2- anthryloxy group, 9-anthryloxy group, 1-
`phenanthryloxy group, 3-phenanthryloxy group, 9-phenanthryloxy group, and the like.
`
`[0060]
`
`The numberof carbon atoms of the arylthioxy group is not particularly limited, but is preferably 5
`to 30, more preferably 6 to 30. Specific examples of the arylthioxy group include a phenylthioxy
`group, a 2-methylphenylthioxy group, a 4-tert-butylphenylthioxy group, and the like, and the
`arylsulfoxy group includes a benzenesulfoxy group, a p-toluenesulfoxy group, etc. it's not going to
`be
`
`[0061]
`
`In the present specification, examples of the arylamine group include a substituted or unsubstituted
`monoarylamine group, or a substituted or unsubstituted diarylamine group. The aryl group in the
`arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group
`including two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, ora
`
`monocyclic aryl group and a polycyclic aryl group at the same time. For example, the aryl group in
`the arylamine group may be selected from the examplesof the aryl group described above.
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`KR20210092513A
`
`[0062]
`
`In the present specification, the heterocyclic group includes atoms other than carbon and one
`or more heteroatoms, specifically, the heteroatoms may include one or more atoms selected
`from the group consisting of O, N, S and P, and the like. The numberof carbon atoms is not
`particularly limited, but preferably has 2 to 50 carbon atoms, further preferably 2 to 30 carbon
`atoms, and the heterocyclic group may be monocyclic or polycyclic. The heterocyclic group may be
`an aromatic ring, an aliphatic ring, and a ring condensed therewith. Examples of the heterocyclic
`group include a thiophene group, a furanyl group, a pyrrole group, an imidazolyl group, a thiazolyl
`group, an oxazolyl group, an oxadiazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl
`group, a triazinyl group, Triazolyl group, acridyl group, pyridazinyl group, pyrazinyl group, quinolyl
`group, quinazolyl group, quinoxalyl group, phthalazinyl group, pyrido pyrimidyl group, pyrido
`
`pyrazinyl group, pyrazino pyrazinyl group group, isoquinolyl group, indolyl group, carbazolyl
`group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group,
`benzothiophene group, dibenzothiophene group, benzofuranyl group, A phenanthroline group, an
`isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but are
`not limited thereto.
`
`[0063]
`
`The heteroaryl group refers to a monovalent aromatic heterocyclic group, and the heteroarylene
`group refers to a divalent aromatic heterocyclic group. The description of the above-mentioned
`heterocyclic group may be cited, except that the heteroaryl group and the heteroarylene group are
`
`aromatic heterocyclic groups.
`
`[0064]
`
`In the present specification, examples of the heteroarylamine group include a substituted or
`unsubstituted monoheteroarylamine group, or a substituted or unsubstituted diheteroarylamine
`group. The heteroarylamine group including two or more heteroaryl groups may include a
`
`monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group
`
`and a polycyclic heteroaryl group at the same time. For example, the heteroaryl group in the
`heteroarylamine group may be selected from the examplesof the heteroaryl group described
`above.
`
`[0065]
`
`In the present specification, examples of the heteroaryl group in the N-arylheteroarylamine group
`and the N-alkylheteroarylamine group are the same as the examplesof the heteroaryl group
`described above.
`
`[0066]
`
`According to an exemplary embodiment of the present specification, Ar is substituted or
`unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl,
`
`substituted or unsubstituted quaterphenyl, substituted or unsubstituted naphthyl , substituted or
`unsubstituted phenanthrenyl, or substituted or unsubstituted triphenylenyl.
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`KR20210092513A
`
`[0067]
`
`According to an exemplary embodiment of the present specification, Ar is phenyl, biphenyl,
`terphenyl, quaterphenyl, naphthyl unsubstituted or substituted with phenyl, phenanthrenyl
`substituted or unsubstituted with phenyl, or triphenylenyl.
`
`[0068]
`
`According to an exemplary embodiment of the present specification, L1 is substituted or
`unsubstituted phenylene, substituted or unsubstituted biphenylrylene, substituted or unsubstituted
`terphenylrylene, substituted or unsubstituted quaterphenylrylene, substituted or unsubstituted
`substituted naphthylene, substituted or unsubstituted phenanthrenylene, or substituted or
`unsubstituted triphenylenylene.
`
`[0069]
`
`According to an exemplary embodiment of the present specification, L1 is phenylene,
`biphenylrylene, terphenylrylene, quaterphenylrylene, naphthylene, phenanthrenylene, or
`triphenylenylene.
`
`[0070]
`
`According to an exemplary embodiment of the present specification, L1 is phenylene, naphthylene,
`phenanthrenylene, or triphenylenylene.
`
`[0071]
`
`According to an exemplary embodiment of the present specification, p is 1 or 2.
`
`[0072]
`
`According to an exemplary embodiment of the present specification, Chemical Formula 1 may be
`represented by Chemical Formula 11 below.
`
`[0073]
`
`[Formula 11]
`
`[0074]
`
`[image]
`
`[0075]
`
`In the formula (11),
`
`[0076]
`
`L1 and L2 are the same asor different from each other, and each independently represents a
`direct bond, or a substituted or unsubstituted arylene group having 5 to 50 carbon atoms, gq andr
`are integers of 1 to 5;
`
`[0077]
`
`Ari and Ar2 are a substituted or unsubstituted aryl group having 5 to 30 carbon atoms,
`
`[0078]
`
`R1 to R8 are as defined in Formula 1.
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`KR20210092513A
`
`[0079]
`
`According to an exemplary embodiment of the present specification, in Formula 11, -(L1)q-Ar1 and
`-(L2)r-Ar2 are different from each other.
`
`[0080]
`
`According to an exemplary embodiment of the present specification, in Formula 11, R1 to R8 are
`hydrogen or deuterium.
`
`[0081]
`
`According to an exemplary embodiment of the present specification, Chemical Formula 1 may be
`represented by the following Chemical Formula 12 or Chemical Formula 13.
`
`[0082]
`
`[Formula 12]
`
`[0083]
`
`[image]
`
`[0084]
`
`[Formula 13]
`
`[0085]
`
`[image]
`
`[0086]
`
`In Formulas 12 and 13,
`
`[0087]
`
`L1 to L3 are the same asor different from each other, each independently a direct bond, or a
`substituted or unsubstituted C5 to C50 arylene group, g, r and s are integers from 1 to 5,
`
`[0088]
`
`Ari to Ar3 are a substituted or unsubstituted aryl group having 5 to 30 carbon atoms,
`
`[0089]
`
`R1 to R8 are as defined in Formula 1.
`
`[0090]
`
`According to an exemplary embodiment of the present specification, in Chemical Formulas 12 and
`13, -(L1)q-Ar1 and -(L2)r-Ar2 are different from each other.
`
`[0091]
`
`According to an exemplary embodiment of the present specification, in Formula 12, R1 to R6 and
`R8 are hydrogen or deuterium.
`
`[0092]
`
`According to an exemplary embodiment of the present specification, in Formula 13, R1 to R7 are
`hydrogen or deuterium.
`
`[0093]
`
`According to an exemplary embodiment of the present specification, Ar1 to Ar3 are the same as
`or different from each other, and are each independently substituted or unsubstituted pheny|,
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`KR20210092513A
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`substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or
`unsubstituted quaterphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted
`phenanthrenyl, or substituted or unsubstituted triphenylenyl.
`
`[0094]
`
`[0095]
`
`According to an exemplary embodiment of the present specification, Ar1 to Ar3 are the same as
`or different from each other, and each independently phenyl, biphenyl, terohenyl, quaterphenyl,
`naphthyl unsubstituted or substituted with phenyl, or unsubstituted with phenyl phenanthrenyl, or
`triphenylenyl.
`
`According to an exemplary embodiment of the present specification, L1 to L8 are the same as or
`different from each other, and are each independently substituted or unsubstituted phenylene,
`substituted or unsubstituted biphenylylene, substituted or unsubstituted terphenylrylene,
`substituted or unsubstituted quaterphenylrylene, substituted or unsubstituted naphthylene,
`substituted or unsubstituted phenanthrenylene, or substituted or unsubstituted triphenylenylene.
`
`[0096]
`
`According to an exemplary embodiment of the present specification, L1 to L3 are the same as or
`different from each other, and each independently phenylene, biphenylrylene, terphenylrylene,
`quaterphenyllylene, naphthylene, phenanthrenylene, or triphenylenylene am.
`
`[0097]
`
`According to an exemplary embodiment of the present specification, L1 to LS are the same
`as or different from each other, and each independently represents phenylene, naphthylene,
`phenanthrenylene, or triphenylenylene.
`
`[0098]
`
`According to an exemplary embodiment of the present specification, p, q andr are each 1 or 2.
`
`[0099]
`
`According to an exemplary embodiment of the present specification, Chemical Formula 1 may be
`selected from the following structural formulas, but is not limited thereto. In addition, when Formula
`1
`is substituted with deuterium, deuterium is not shown in the following structural formulas, but
`10% to 100% of the number of hydrogen bonds in the following structural formulas includes a
`structure in which deuterium is substituted.
`
`[0100]
`
`[image]
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`[0101]
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`[image]
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`KR20210092513A
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`[0102]
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`[image]
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`[0103]
`
`[image]
`
`[0104]
`
`[image]
`
`[0105]
`
`[image]
`
`[0106]
`
`[image]
`
`[0107]
`
`[image]
`
`[0108]
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`[image]
`
`[0109]
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`[image]
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`[0110]
`
`According to an exemplary embodiment of the present specification, the compound of Formula 1
`in which deuterium is substituted may be selected from the following structural formulas, but is not
`limited thereto.
`
`[0111]
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`[image]
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`[0112]
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`[image]
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`[0113]
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`[image]
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`[0114]
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`[image]
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`[0115]
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`[image]
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`[0116]
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`[image]
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`[0117]
`
`[image]
`
`[0118]
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`[image]
`
`[0119]
`
`According to an exemplary embodiment of the present specification, one of the two typesof
`hosts is represented by a compound of Formula 3 below, and the other one is represented by a
`compound of Formula 4 below.
`
`[0120]
`
`[Formula 3]
`
`[0121]
`
`[image]
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`[0122]
`
`[Formula 4]
`
`[0123]
`
`[image]
`
`[0124]
`
`In Formulas 3 and 4, a, c, d and f are each an integer of 0 to 7, b and e are each anintegerof 0 to
`8, gis an integer of 1 to 3, and L2 is substituted with deuterium or an unsubstituted arylene group
`having 6 to 30 carbon atoms, and the sum of the number of deuterium contained in Chemical
`Formula 3 and the number of deuterium contained in Chemical Formula 4 is 1 or more.
`
`[0125]
`
`In one example, L2 is phenylene unsubstituted or substituted with deuterium.
`
`[0126]
`
`According to an exemplary embodiment of the present specification, when one of the hosts
`includes a compound having a deuterium substitution rate of 10 to 100% of Formula 1, and the
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`KR20210092513A
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`[0127]
`
`[0128]
`
`deuterium substitution rate is less than 10%, synthesis is difficult, and when applied to a device,
`the effect of life improvement is it is incomplete
`
`In an exemplary embodiment of the present specification, one of the hosts includes a compound
`having a deuterium substitution rate of 40 to 100%of Formula 1. When a compoundhaving a
`deuterium substitution ratio of 40 to 100%is used, the effect of improving lifespan when applied to
`a device is very excellent.
`
`According to an exemplary embodiment of the present specification, two of the hosts include a
`compound having a deuterium substitution rate of 10 to 100% of Formula 1. Whentwoof the hosts
`have a deuterium substitution rate of 10 to 100%in Formula 1, the device has excellent efficiency
`and lifetime.
`
`[0129]
`
`According to an exemplary embodiment of the present specification, the massratio of the two
`hosts is 1:9 to 9:1.
`
`[0130]
`
`According to an exemplary embodiment of the present specification, the dipole moment (DMhost)
`value of the hostof the light emitting layer is less than 0.5, respectively. Since the anthracene
`derivative of Chemical Formula 1, which is composed of a bond between carbon and hydrogen
`and a bond between carbon and deuterium, does not contain a heteroatom increasing the dipole
`moment, the dipole moment (DMhost) value is less than 0.5. When two types of hosts having a
`dipole moment (DM) value of less than 0.5 are combined, the dispersing power of the mixed host
`to the film and the dispersing powerof the host of the other species are excellent, thereby leading
`to excellent performance and high stability of the device.
`
`[0131]
`
`In the present specification, the dipole moment (dipole moment) is a physical quantity indicating
`the degreeof polarity, it can be calculated by Equation 1 below, and the unit is debye (D).
`
`[0132]
`
`[Equation 1]
`
`[0133]
`
`[image]
`
`[0134]
`
`By calculating the molecular density in Equation 1 above, the value of the dipole moment can be
`obtained. For example, the molecular density can be obtained by obtaining the charge and dipole
`of each atom using a method called Hirshfeld Charge Analysis, and calculating it according to
`the following equation, and putting the calculation result in Equation 1 above, the dipole moment
`(Dipole Moment) can be obtained.
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`[0135]
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`[image]
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`KR20210092513A
`
`[0136]
`
`According to an exemplary embodiment of the present specification, it is preferable that the dipole
`moment DMhost1 of the first host and the dipole moment DMhosiz2of the second hostof the light
`emitting layer satisfy Equation 1 below. Since the anthracene derivative of Formula 1, whichis
`composedof a bond between carbon and hydrogen, and a bond between carbon and deuterium,
`does not contain a heteroatom that increases the dipole moment, the dipole moment (DMhost)
`value is less than 0.5, and two types of mixed hosts. When the dipole moment value satisfies the
`following range, the stability of the device is increased.
`
`[0137]
`
`[Equation 1]
`
`[0138]
`
`|DMhost1 - DMhost2| < 0.2
`
`[0139]
`
`According to an exemplary embodiment of the present specification, the organic
`electroluminescent device is a multi-stack type, and one or two