KR20210092513A - Organic electroluminescent device - Google Patents

Abstract

The present specification relates to an organic electroluminescent element. The organic electroluminescent element includes a cathode; an anode; and a light emitting layer provided between the cathode and the anode. Element efficiency, driving voltage characteristics, or lifespan characteristics can be improved.

Description

Organic electroluminescent device {ORGANIC ELECTROLUMINESCENT DEVICE}

The present specification relates to an organic electroluminescent device.

The organic electroluminescent device has a structure in which an organic thin film is disposed between two electrodes. When a 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 compounds in which organic materials and metals are complexed account for most, and depending on the use, hole injection material, hole transport material, light emitting material, electron transport material, 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, that is, 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 converts it into light when it is formed is preferable.

In order to improve the performance, lifespan or efficiency of an organic electroluminescent device, the development of a material for an organic thin film is continuously required.

Korean Publication No. 10-2013-117449

The present specification provides an organic electroluminescent device.

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 the hosts is deuterium It provides an organic electroluminescent device having a substitution rate of 10% to 100%.

[Formula 1]

In Formula 1,

At least one of R1 to R10 is Formula 2,

[Formula 2]

Among R1 to R10, 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 carbon number From the group consisting of a 3 to 30 cycloalkyl group, a substituted or unsubstituted C 1 to C 30 alkylsilyl group, a substituted or unsubstituted C 5 to C 30 arylsilyl group, a cyano group, a nitro group, a hydroxyl group and a halogen group. selected,

* in Formula 2 represents a connection site with at least one of R1 to R10,

L1 is a direct bond, or a substituted or unsubstituted arylene group having 5 to 50 carbon atoms,

p is an integer from 1 to 5,

Ar is a substituted or unsubstituted aryl group having 5 to 30 carbon atoms.

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.

1 and 3 show an organic electroluminescent device according to an exemplary embodiment of the present specification.
2 is a TLC-MS graph for calculating the deuterium substitution rate.

Hereinafter, the present specification will be described in detail.

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 Formula 1, and at least one of the hosts is deuterium It is characterized in that the substitution rate is 10% to 100%.

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.

Specifically, anthracene derivatives containing an aryl-based substituent have stable performance when used as a host for an organic electroluminescent device, and thus have been commercialized to date. However, a single host has opposite effects of lifetime and efficiency, so it was difficult to satisfy both. As an alternative, a mixed host has been used, but it is difficult to improve the performance of the fabricated color device because it cannot deviate from the basic performance range of organic compounds.

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. In the present specification, by introducing an aryl-based anthracene derivative substituted with deuterium as a mixed host, the organic electric field 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.

zero point energy =

The light emitting layer of the organic electroluminescent device is a region having a direct influence on 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 carbon-hydrogen bonds of a certain ratio or more with carbon-deuterium bonds, the binding energy of molecules can be increased, thereby improving the lifespan of the organic electroluminescent device.

In the present specification, when a part "includes" a certain component, this means that other components may be further included rather than excluding other components unless otherwise stated.

In the present specification, the deuterium substitution ratio refers to a substitution ratio of deuterium in a molecule, and the following two methods are followed 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.

1. TLC-MS (Thin-Layer Chromatography/Mass Spectrometry) is used (synthesis process confirmation method)

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.

For example, in the case of the compound shown in 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%.

2. Quantitative analysis using NMR

DMF is added as an internal standard, and the D substitution rate can be calculated from the integral amount of 　 total 　 peak using the integration ratio on 1H　NMR.

Examples of substituents in the present specification are described below, but are not limited thereto.

The term "substitution" means that a hydrogen atom bonded to 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 substituted. , two or more substituents may be the same as or different from each other.

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 that it is substituted with one or two or more 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 may be interpreted as a substituent in which two phenyl groups are connected.

In the present specification, the halogen group may be fluorine, chlorine, bromine or iodine.

In the present specification, the alkyl group may be linear or branched, and the number of 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-ethylbutyl, 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.

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 be a 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 be It is not limited.

In the present specification, the amine group is -NH ₂ ; 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 group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, N-bi Phenylnaphthylamine group, N-naphthylfluorenylamine group, N-phenylphenanthrenylamine group, N-biphenylphenanthrenylamine group, N-phenylfluorenylamine group, N-phenylterphenylamine group group, N-phenanthrenylfluorenylamine group, N-biphenylfluorenylamine group, and the like, but is not limited thereto.

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.

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.

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.

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.

The number of 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 octyltioxy group, and the like, and the alkylsulfoxy group includes a mesyl, an ethylsulfoxy group, a propylsulfoxy group, a butylsulfoxy group, and the like, The present invention is not limited thereto.

In the present specification, the alkenyl group may be linear or branched, and the number of 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, stilbenyl group, styrenyl group, and the like, but is not limited thereto.

In the present specification, the alkynyl group may be linear 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.

In the present specification, the silyl group may be an alkylsilyl group or an arylsilyl group, and further may be a trialkylsilyl group or a triarylsilyl group. The number of carbon atoms of the silyl 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, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc., but is not limited thereto. .

In the present specification, the boron group _{may be -BR 100} R ₁₀₁ , wherein R ₁₀₀ and R ₁₀₁ 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.

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.

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.

When the 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.

When the aryl group is a polycyclic aryl group, the number of 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 phenalenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, a fluoranthenyl group, etc. , but is not limited thereto.

In the present specification, the fluorenyl group may be substituted, and adjacent groups may combine with each other to form a ring.

,

,

,

,

및

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

,

,

,

and

etc. can be However, the present invention is not limited thereto.

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.

The number of 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-trimethylphenoxy 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.

The number of 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 and a p-toluenesulfoxy group, but are limited thereto. it's not going to be

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, or a 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 examples of the aryl group described above.

In the present specification, the heterocyclic group includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, S and P, and the like. The number of 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, or 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, pyridopyrimidyl group, pyridopyrazinyl group, pyrazinopyrazinyl 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.

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.

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 examples of the heteroaryl group described above.

In the present specification, examples of the heteroaryl group in the N-arylheteroarylamine group and the N-alkylheteroarylamine group are the same as the examples of the heteroaryl group described above.

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.

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.

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.

According to an exemplary embodiment of the present specification, L1 is phenylene, biphenylrylene, terphenylrylene, quaterphenylrylene, naphthylene, phenanthrenylene, or triphenylenylene.

According to an exemplary embodiment of the present specification, L1 is phenylene, naphthylene, phenanthrenylene, or triphenylenylene.

According to an exemplary embodiment of the present specification, p is 1 or 2.

According to an exemplary embodiment of the present specification, Chemical Formula 1 may be represented by Chemical Formula 11 below.

[Formula 11]

In Formula 11,

L1 and L2 are the same as or different from each other, each independently a direct bond, or a substituted or unsubstituted C5 to C50 arylene group, q and r are integers from 1 to 5,

Ar1 and Ar2 are a substituted or unsubstituted aryl group having 5 to 30 carbon atoms,

R1 to R8 are as defined in Formula 1.

According to an exemplary embodiment of the present specification, in Formula 11, -(L1)q-Ar1 and -(L2)r-Ar2 are different from each other.

According to an exemplary embodiment of the present specification, in Formula 11, R1 to R8 are hydrogen or deuterium.

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.

[Formula 12]

[Formula 13]

In Formulas 12 and 13,

L1 to L3 are the same as or different from each other, each independently a direct bond, or a substituted or unsubstituted arylene group having 5 to 50 carbon atoms, q, r and s are integers of 1 to 5;

Ar1 to Ar3 are a substituted or unsubstituted aryl group having 5 to 30 carbon atoms,

R1 to R8 are as defined in Formula 1.

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.

According to an exemplary embodiment of the present specification, in Formula 12, R1 to R6 and R8 are hydrogen or deuterium.

According to an exemplary embodiment of the present specification, in Formula 13, R1 to R7 are hydrogen or deuterium.

According to an exemplary embodiment of the present specification, Ar1 to Ar3 are the same as or different from each other, and each independently represent a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted quaternaryphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, or substituted or unsubstituted triphenylenyl.

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, terphenyl, 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 L3 are the same as or different from each other, and 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.

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.

According to an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently represents phenylene, naphthylene, phenanthrenylene, or triphenylenylene.

According to an exemplary embodiment of the present specification, p, q and r are each 1 or 2.

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.

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.

According to an exemplary embodiment of the present specification, one of the two types of hosts is represented by a compound of Formula 3 below, and the other one is represented by a compound of Formula 4 below.

[Formula 3]

[Formula 4]

In Formulas 3 and 4, a, c, d and f are each an integer of 0 to 7, b and e are each an integer of 0 to 8, g is 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.

In one example, L2 is phenylene unsubstituted or substituted with deuterium.

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 deuterium substitution rate is less than 10%, synthesis is difficult, and the effect of life improvement when applied to a device 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 compound having 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. When two of the hosts have a deuterium substitution rate of 10 to 100% in Formula 1, the device has excellent efficiency and lifespan.

According to an exemplary embodiment of the present specification, the mass ratio of the two hosts is 1:9 to 9:1.

According to an exemplary embodiment of the present specification, the dipole moment (DM _host ) value of the host of 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 (DM _host ) 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 power of the host of the other species are excellent, thereby leading to excellent performance and high stability of the device.

In the present specification, the dipole moment (dipole moment) is a physical quantity indicating the degree of polarity, it can be calculated by Equation 1 below, and the unit is debye (D).

[Equation 1]

The value of the dipole moment can be obtained by calculating the molecular density in Equation 1 above. 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 into Equation 1 above, the dipole moment (Dipole Moment) can be found.

According to an exemplary embodiment of the present specification, _{it is preferable that the dipole moment of the first host (DM host1} ) and the dipole moment of the second host (DM _host2 ) of the emission layer satisfy Equation 1 below. Since the anthracene derivative of Formula 1, which is composed of 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 (DM _host ) value is less than 0.5, and two types of mixed hosts When the dipole moment value of , satisfies the following range, the stability of the device is increased.

[Equation 1]

|DM _host1 - DM _host2 | < 0.2

According to an exemplary embodiment of the present specification, the organic electroluminescent device is a multi-stack type, and one or two stacks of them include the two kinds of hosts.

According to an exemplary embodiment of the present specification, the emission spectrum of the emission layer including the two types of hosts and one type of dopant has λmax within 400 nm to 470 nm.

According to an exemplary embodiment of the present specification, the dopant is a fluorescent dopant.

According to an exemplary embodiment of the present specification, the dopant includes a pyrene-based compound.

According to another exemplary embodiment, the dopant includes a pyrene-based compound unsubstituted or substituted with deuterium.

According to an exemplary embodiment of the present specification, the dopant includes a non-pyrene-based compound.

According to another exemplary embodiment, the dopant includes a non-pyrene-based compound substituted or unsubstituted with deuterium.

According to an exemplary embodiment of the present specification, the non-pyrene-based compound includes a boron-based compound.

According to another exemplary embodiment, the non-pyrene-based compound includes a boron-based compound substituted or unsubstituted with deuterium.

The organic material layer of the organic electroluminescent device of the present specification may have a single-layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, as a representative example of the organic light emitting device of the present specification, the organic electroluminescent device may include only one light emitting layer as an organic material layer, but in addition to the light emitting layer, a hole injection layer, a hole transport layer, a hole control layer, an electron transport layer, an electron injection layer, It may have a structure including an electron control layer and the like.

In one embodiment of the present specification, the organic light emitting device may be an organic light emitting device of a structure (normal type) in which an anode, one or more organic material layers and a cathode are sequentially stacked on a substrate.

In an exemplary embodiment of the present specification, the organic light emitting device may be an organic light emitting device of an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.

For example, the structure of the organic electroluminescent device according to an embodiment of the present specification is illustrated in FIG. 1 . 1 and 3 illustrate an organic electroluminescent device, but is not limited thereto.

1 illustrates a structure of an organic electroluminescent device 10 in which a substrate 20, an anode 30, a light emitting layer 40, and a cathode 50 are sequentially stacked.

3 shows a substrate 20, an anode 30, a hole injection layer 60, a hole transport layer 70, a hole control layer 80, a light emitting layer 40, an electron control layer 90, an electron transport layer 100. , the electron injection layer 110 , the cathode 50 and the capping layer 120 are sequentially stacked and the structure of the organic electroluminescent device is exemplified.

The organic electroluminescent device of the present specification may be manufactured using materials and methods known in the art, except that at least one light emitting layer includes the above-described two types of hosts and one type of dopant.

When the organic electroluminescent device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

For example, the organic electroluminescent device according to the present specification uses a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, to form a metal or a metal oxide having conductivity on a substrate or a metal oxide or these An anode is formed by depositing an alloy, and an organic material layer including at least one of a hole injection layer, a hole transport layer, a hole control layer, a light emitting layer, an electron transport layer, an electron injection layer, and an electron control layer is formed thereon. It can be prepared by depositing a material that can be used as In addition to this method, an organic electroluminescent device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

The organic material layer includes a hole injection layer, a hole transport layer, a layer that injects and transports holes at the same time, an electron control layer, a hole control layer, a light emitting layer, an electron transport layer, an electron injection layer, and a layer that simultaneously injects and transports electrons. It may have a multi-layer structure, but is not limited thereto and may have a single-layer structure. In addition, the organic layer is formed using a variety of polymer materials in a smaller number by a solvent process rather than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer method. It can be made in layers.

The anode is an electrode for injecting holes, and as the anode material, a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO ₂ : Combination of metals and oxides such as Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

The cathode is an electrode for injecting electrons, and the cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; and a multilayer structure material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

The hole injection layer is a layer that facilitates the injection of holes from the anode to the light emitting layer. As the hole injection material, holes can be well injected from the anode at a low voltage, and the highest occupied (HOMO) of the hole injection material is The molecular orbital) is preferably between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based organic material. of organic substances, anthraquinones, and conductive polymers of polyaniline and polythiophene series, but are not limited thereto.

The hole transport layer may serve to facilitate hole transport. As the hole transport material, a material capable of receiving holes from the anode or hole injection layer and transferring them to the light emitting layer is suitable, and a material having high hole mobility is suitable. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.

A hole control layer may be provided between the hole transport layer and the light emitting layer. For the hole control layer, a material known in the art may be used.

An electron control layer may be provided between the electron transport layer and the light emitting layer. For the electron control layer, a material known in the art may be used.

The light emitting layer may emit red, green or blue light, and may be formed of a phosphorescent material or a fluorescent material. The light emitting material is a material capable of emitting light in the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable.

Examples of host materials for the light emitting layer other than the two types of hosts described above include condensed aromatic ring derivatives or heterocyclic compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

When the emission layer emits red light, the emission dopant is PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium) ), a phosphorescent material such as octaethylporphyrin platinum (PtOEP), or a _{fluorescent material such as Alq 3} (tris(8-hydroxyquinolino)aluminum) may be used, but is not limited thereto. When the emission layer emits green light, the emission dopant is a _{phosphor such as Ir(ppy) 3} (fac tris(2-phenylpyridine)iridium), Alq ₃ (tris(8-hydroxyquinolino)aluminum), anthracene-based compound, or pi A fluorescent material such as a lene-based compound or boron-based compound may be used, but is not limited thereto. When the light emitting layer emits blue light, the light emitting dopant includes a _{phosphorescent material such as (4,6-F2ppy) 2} Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), distrylarylene (DSA), A fluorescent material such as a PFO-based polymer, a PPV-based polymer, an anthracene-based compound, a pyrene-based compound, or a boron-based compound may be used, but is not limited thereto.

The electron transport layer may serve to facilitate the transport of electrons. As the electron transport material, a material capable of well injecting electrons from the cathode and transferring them to the light emitting layer, and a material having high electron mobility is suitable. Specific examples include Al complex of 8-hydroxyquinoline; complexes containing Alq _{3 ;} organic radical compounds; hydroxyflavone-metal complexes and the like, but are not limited thereto.

The electron injection layer may serve to facilitate injection of electrons. The electron injection material has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, prevents the movement of excitons generated in the light emitting layer to the hole injection layer, and , a compound having excellent thin film forming ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc., derivatives thereof, metals complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-crezolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. However, the present invention is not limited thereto.

The organic electroluminescent device according to the present invention may be a top emission type, a back emission type, or a double-sided emission type depending on the material used.

Hereinafter, the present specification will be described in more detail through examples. However, the following examples are only for illustrating the present specification, and not for limiting the present specification.

[Production Example]

The reactant (leq), Trifluoromethanesulfonic acid (cat.) was put in C ₆ D ₆ (10-50 times the mass ratio of the reactant) and stirred at 70° C. for 1 to 100 minutes. After completion of the reaction, D ₂ O (excess) was added and stirred for 30 minutes, followed by dropwise addition of trimethylamine (excess). The reaction solution was transferred to a separatory funnel, and extracted with water and chloroform. The extract _{was dried over MgSO 4} , and recrystallized by heating with toluene to obtain the products shown in Table 1 below.

practice
heavy hydrogen
compound reactant product reactant
m/z product theory
max m/z reaction
time
(min) product
real
max m/z entire
number of hydrogens D substitution
Count D substitution
ratio (%) synthesis
yield
(%) compound
1-1

[BH1]

506 531 50 530 25 24 96% 70% compound
1-2 [BH2]

430 452 50 452 22 22 100% 73% compound
1-3 [BH3]

456 480 45 473 24 17 71% 74% compound
1-4 [BH4]

430 452 30 443 22 13 59% 69% compound
1-5 [BH5]

506 532 40 522 26 16 62% 65% compound
1-6 [BH6]

430 452 40 448 22 18 82% 70% compound
1-7 [BH7]

456 480 50 478 24 22 92% 73% compound
1-8 [BH8]

456 480 25 468 24 12 50% 71% compound
1-9 [BH9]

456 480 40 477 24 21 88% 68% compound
1-10 [BH10]

456 480 50 477 24 21 88% 65% compound
1-11 [BH11]

456 480 50 476 24 20 83% 70% compound
1-12 [BH12]

506 532 50 529 26 23 88% 66% compound
1-13 [BH13]

532 560 30 551 28 19 68% 72% compound
1-14 [BH14]

532 560 40 556 28 24 86% 71% compound
1-15 [BH15]

456 480 60 480 24 24 100% 73% compound
1-16 [BH16]

482 507 35 500 25 18 72% 65% compound
1-17 [BH17]

430 452 50 447 22 17 77% 66% compound
1-18 [BH18]

506 532 60 530 26 24 92% 71% compound
1-19 [BH19]

480 503 45 498 23 18 78% 70% compound
1-20 [BH20]

530 555 45 549 25 19 76% 68% compound
1-21 [BH21]

556 584 50 580 28 24 86% 64% compound
1-22 [BH1]

506 531 3 512 25 6 24% 70% compound
1-23 [BH2]

430 452 3 435 22 5 23% 73% compound
1-24 [BH10]

456 480 5 463 24 7 29% 65% compound
1-25 [BH16]

482 507 7 492 25 10 40% 65%

Each product had a different degree of deuterium substitution depending on the reaction time, and the substitution rate was determined according to the maximum m/z (M+) value.

The reactants are JP 4070676 B2, KR 1477844 B1, US 6465115 B2, JP 3148176 B2, JP 4025136 B2, JP 4188082 B2, JP 5015459 B2, KR 1979037 B1, KR 1550351 B1, KR 1503766 B1, KR 0826364 B1, KR KR , KR 1115255 B1 was synthesized with reference to prior literature. Also, for the substitution of deuterium for the above product, the prior literature of KR1538534 B1 was referred.

Deuterium (-D) bound to the product synthesized in Table 1 means that it can be bound to the indicated position, and does not necessarily mean that it must be bound to the indicated position.

[ comparative example One] OLED manufacture of

A substrate on which ITO/Ag/ITO was deposited to a thickness of 70/1000/70 Å as an anode was cut into a size of 50 mm x 50 mm x 0.5 mm, and the dispersant was dissolved in distilled water and washed with ultrasonic waves. The detergent used was a product of Fischer Co., and the distilled water was manufactured by Millipore Co. Secondary filtered distilled water was used as a filter of the product. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, and methanol, followed by drying.

On the prepared anode, HI-1 was thermally vacuum deposited to a thickness of 50 Å to form a hole injection layer, and HT1, a material for transporting holes, was vacuum-deposited thereon to a thickness of 1150 Å to form a hole transport layer. Then, a hole control layer was formed using EB1 (150 Å), and then, as a mixed host, BH1 and BH2 (1:1 weight ratio) and dopant BD1 (2 weight %) of Table 1 were vacuumed to a thickness of 360 Å. A light emitting layer was formed by vapor deposition. Thereafter, HB1 was deposited by 50 Å to form an electron control layer, and the compound ET1 and Liq were mixed in a ratio of 5:5 (mass ratio) to form an electron transport layer having a thickness of 250 Å. After sequentially forming a film of 50 Å thick magnesium and lithium fluoride (LiF) as an electron injection layer, 200 Å of magnesium and silver (1:4) were formed as a cathode, and 600 Å of CP1 was deposited (capping layer) to complete the device. . In the above process, the deposition rate of the organic material was maintained at 1 Å/sec.

[ comparative example 2 to 32 and Example 1 to 44]

A device was manufactured in the same manner as in Comparative Example 1, except that the materials shown in Table 2 below were used for the material of the light emitting layer in Comparative Example 1.

For the devices manufactured in Comparative Examples 1 to 32 and Examples 1 to 44 at ^{a current density of 20 mA/cm 2} , the driving voltage, luminous efficiency, color coordinates, and time (LT95) to become 95% compared to the initial luminance were measured. The results are shown in Table 2 below.

Experimental example
20 mA/cm2 light emitting layer device result host
(mixed weight ratio) dopant Voltage (V)
(@20mA/cm ² ) Cd/A
(@20mA/cm ² ) color coordinates
(x,y) life span
(T95, h)
(@20mA/cm ² ) comparative example
One BH1:BH2
(1:1) BD1 4.53 5.02 (0.135, 0.138) 40.5 comparative example
2 BH1:BH4
(1:1) BD1 4.51 4.88 (0.135, 0.138) 43.1 comparative example
3 BH1:BH12
(1:1) BD2 4.60 5.12 (0.136, 0.120) 31.8 comparative example
4 BH2:BH3
(1:1) BD1 4.58 4.81 (0.135, 0.138) 42.6 comparative example
5 BH2:BH5
(1:1) BD1 4.55 4.66 (0.135, 0.138) 45.8 comparative example
6 BH2:BH14
(1:1) BD2 4.48 5.20 (0.136, 0.120) 30.1 comparative example
7 BH3:BH6
(1:1) BD1 4.62 4.89 (0.135, 0.138) 41.3 comparative example
8 BH3:BH11
(1:1) BD1 4.54 4.70 (0.135, 0.138) 43.2 comparative example
9 BH3:BH15
(1:1) BD2 4.56 5.33 (0.136, 0.120) 32.4 comparative example
10 BH4:BH7
(1:1) BD1 4.43 4.92 (0.135, 0.138) 38.4 comparative example
11 BH4:BH13
(1:1) BD1 4.65 4.80 (0.135, 0.138) 40.1 comparative example
12 BH4:BH17
(1:1) BD2 4.83 5.30 (0.136, 0.120) 35.4 comparative example
13 BH5:BH8
(1:1) BD1 4.60 4.94 (0.135, 0.138) 43.9 comparative example
14 BH5:BH9
(1:1) BD1 4.55 4.74 (0.135, 0.138) 50.5 comparative example
15 BH5:BH14
(1:1) BD2 4.44 5.20 (0.136, 0.120) 32.3 comparative example
16 BH6:BH10
(1:1) BD1 4.48 4.90 (0.135, 0.138) 49.3 comparative example
17 BH6:BH16
(1:1) BD1 4.52 4.80 (0.135, 0.138) 44.7 comparative example
18 BH6:BH19
(1:1) BD2 4.61 5.38 (0.136, 0.120) 31.3 comparative example
19 BH7:BH18
(1:1) BD1 4.66 5.08 (0.135, 0.138) 42.9 comparative example
20 BH7:BH20
(1:1) BD1 4.51 4.94 (0.135, 0.138) 48.4 comparative example
21 BH7:BH21
(1:1) BD2 4.58 5.41 (0.136, 0.120) 28.4 comparative example
22 BH8:BH14
(2:1) BD1 4.62 4.93 (0.135, 0.138) 51.3 comparative example
23 BH9:BH21
(2:1) BD1 4.58 5.01 (0.135, 0.138) 46.2 comparative example
24 BH11:BH17
(3:1) BD2 4.60 5.44 (0.136, 0.120) 38.3 comparative example
25 BH15:BH16
(2:1) BD1 4.46 4.83 (0.135, 0.138) 50.8 comparative example
26 BH18:BH21
(4:1) BD2 4.71 5.42 (0.136, 0.120) 40.5 comparative example
27 BH1 BD1 4.62 4.73 (0.135, 0.138) 30.2 comparative example
28 BH2 BD2 4.70 4.82 (0.136, 0.120) 23.3 comparative example
29 Formula 1-1 BD1 4.78 4.65 (0.136, 0.120) 53.8 comparative example
30 Formula 1-14 BD2 4.77 4.80 (0.136, 0.120) 50.1 comparative example
31 BH1:BH22
(1:1) BD1 4.57 4.32 (0.135, 0.138) 22.8 comparative example
32 BH23: Compound 1-1
(1:1) BD1 4.58 4.28 (0.135, 0.138) 21.0 Example
One BH1: Compound 1-1
(1:1) BD1 4.55 5.03 (0.135, 0.138) 60.3 Example
2 BH2: compound 1-3
(1:1) BD1 4.53 5.02 (0.135, 0.138) 63.8 Example
3 BH4: compound 1-18
(1:1) BD1 4.58 4.93 (0.135, 0.138) 59.4 Example
4 BH5: compound 1-4
(1:1) BD1 4.56 4.77 (0.135, 0.138) 63.1 Example
5 BH7: compound 1-4
(1:1) BD1 4.58 4.80 (0.135, 0.138) 60.2 Example
6 BH8: compound 1-12
(1:1) BD1 4.61 4.74 (0.135, 0.138) 62.8 Example
7 BH10: compound 1-21
(1:1) BD1 4.65 4.67 (0.135, 0.138) 58.3 Example
8 BH11: compound 1-11
(1:1) BD1 4.60 4.79 (0.135, 0.138) 61.5 Example
9 BH13: compound 1-11
(1:1) BD1 4.73 4.92 (0.135, 0.138) 59.1 Example
10 BH14: compound 1-16
(1:1) BD1 4.68 4.84 (0.135, 0.138) 60.5 Example
11 BH16: compound 1-6
(1:1) BD1 4.63 4.79 (0.135, 0.138) 63.1 Example
12 BH17: compound 1-10
(1:1) BD1 4.71 4.99 (0.135, 0.138) 61.4 Example
13 BH19: compound 1-15
(1:1) BD1 4.58 4.80 (0.135, 0.138) 62.3 Example
14 BH20: compound 1-17
(1:1) BD1 4.76 4.91 (0.135, 0.138) 62.8 Example
15 BH1: compound 1-22
(1:1) BD1 4.55 5.03 (0.135, 0.138) 55.4 Example 16 BH16: compound 1-6
(2:1) BD1 4.68 4.90 (0.135, 0.138) 58.4 Example
17 BH5: compound 1-4
(1:3) BD1 4.60 4.80 (0.135, 0.138) 60.1 Example
18 Compound 1-1: Compound 1-2
(1:1) BD1 4.53 5.01 (0.135, 0.138) 80.4 Example
19 Compound 1-1: Compound 1-4
(1:1) BD1 4.70 5.03 (0.135, 0.138) 74.5 Example
20 Compound 1-2: Compound 1-7
(1:1) BD2 4.68 5.43 (0.136, 0.120) 63.7 Example
21 Compound 1-2: Compound 1-13
(1:1) BD1 4.64 4.83 (0.135, 0.138) 75.9 Example
22 Compound 1-3: Compound 1-8
(1:1) BD1 4.66 4.88 (0.135, 0.138) 78.3 Example
23 Compound 1-3: Compound 1-20
(1:1) BD2 4.70 4.92 (0.136, 0.120) 80.1 Example
24 Compound 1-4: Compound 1-8
(1:1) BD1 4.61 4.84 (0.135, 0.138) 79.5 Example
25 Compound 1-4: Compound 1-11
(1:1) BD1 4.68 4.88 (0.135, 0.138) 78.5 Example
26 Compound 1-6: Compound 1-5
(1:1) BD2 4.59 5.35 (0.136, 0.120) 60.5 Example
27 Compound 1-5: Compound 1-16
(1:1) BD1 4.67 4.90 (0.135, 0.138) 79.8 Example
28 Compound 1-6: Compound 1-9
(1:1) BD1 4.73 4.82 (0.135, 0.138) 80.5 Example
29 Compound 1-6: Compound 1-12
(1:1) BD2 4.65 5.44 (0.136, 0.120) 59.4 Example
30 Compound 1-7: Compound 1-15
(1:1) BD1 4.70 4.95 (0.135, 0.138) 75.6 Example
31 Compound 1-7: Compound 1-21
(1:1) BD1 4.61 4.88 (0.135, 0.138) 74.9 Example
32 Compound 1-8: Compound 1-10
(1:1) BD2 4.66 5.38 (0.136, 0.120) 58.1 Example
33 Compound 1-8: Compound 1-17
(1:1) BD1 4.59 4.91 (0.135, 0.138) 78.4 Example
34 Compound 1-9: Compound 1-17
(1:1) BD1 4.71 4.89 (0.135, 0.138) 77.3 Example
35 Compound 1-10: Compound 1-14
(1:1) BD2 4.62 5.34 (0.136, 0.120) 58.1 Example
36 Compound 1-10: Compound 1-18
(1:1) BD1 4.53 5.01 (0.135, 0.138) 81.1 Example
37 Compound 1-11: Compound 1-19
(1:1) BD1 4.63 4.73 (0.135, 0.138) 78.6 Example
38 Compound 1-4: Compound 1-11
(2:1) BD1 4.68 4.93 (0.135, 0.138) 73.1 Example
39 Compound 1-7: Compound 1-21
(3:1) BD1 4.58 4.77 (0.135, 0.138) 75.8 Example
40 Compound 1-10: Compound 1-18
(2:1) BD1 4.70 5.12 (0.135, 0.138) 77.2 Example
41 Compound 1-1: Compound 1-22
(1:1) BD1 4.71 4.89 (0.135, 0.138) 70.1 Example
42 Compound 1-3: Compound 1-23
(1:1) BD1 4.66 5.01 (0.135, 0.138) 69.1 Example
43 Compound 1-18: Compound 1-25
(1:1) BD1 4.63 4.93 (0.135, 0.138) 68.2 Example
44 Compound 1-22: Compound 1-24
(1:1) BD1 4.70 4.91 (0.135, 0.138) 67.9

The mixed host applied to the blue host of the light emitting layer of the blue organic electroluminescent device according to the present invention contains two or more compounds of Formula 1, at least one of which is a chemical structure including a compound in which 10 to 100% of deuterium is substituted The performance of the organic electroluminescent device is improved based on the stability of the present invention, and in particular, it shows excellent characteristics in terms of the lifespan of the blue light emitting device, which has been an issue for over 10 years. It also shows that the voltage, efficiency, and lifetime of the device can be controlled by controlling the mixing ratio of the host.

Examples 1 to 17 include the compound of Formula 1 in which one of the blue mixed hosts of the light emitting layer is substituted with deuterium, which shows an average lifespan increase of 10 to 30% compared to Comparative Examples 1 to 32. Regardless of the application of BD1, which is a pyrene-based blue dopant, and BD2, which is a representative blue dopant of non-pyrene series, a constant device lifetime improvement result is shown.

In particular, Examples 1 to 44 are Comparative Examples 29 and 30 (when only one compound of Formula 1 is included as a host), Comparative Example 31 (One of the two hosts is a heteroaryl-substituted anthracene compound, and the other one is not deuterium substituted It can be seen that the performance of the manufactured device is excellent compared to the case of the compound of Formula 1) and Comparative Example 32 (when one compound of Formula 1 in which deuterium is substituted as a host and one heteroaryl host is included).

In particular, in Example 1 of the present application, by using two types of compounds of Formula 1 (at least one type is deuterium substituted) as a host of the light emitting layer, compared to Comparative Example 29 including only one compound of Formula 1 as a host, the voltage and efficiency are greatly improved. can confirm. In addition, Comparative Example 32 shows a large drop in the efficiency and lifespan of the device compared to Example 1 of the present application by using a heteroaryl host with a marked difference in the balance of carriers compared to the aryl-based host, in particular, injection of holes into the light emitting layer. there is.

Examples 18 to 44 are examples of using two kinds of compounds of Formula 1 substituted with deuterium as a blue mixed host, and it can be confirmed that they have superior effects than the devices of Comparative Examples 1 to 32.

10: organic electroluminescent device
20: substrate
30: anode
40: light emitting layer
50: cathode
60: hole injection layer
70: hole transport layer
80: hole control layer
90: electronic control layer
100: electron transport layer
110: electron injection layer
120: capping layer

Claims (15)

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, and at least one of the hosts is deuterium An organic electroluminescent device having a substitution ratio of 10% to 100%:
[Formula 1]

In Formula 1,
At least one of R1 to R10 is Formula 2,
[Formula 2]

Among R1 to R10, groups not bonded to Formula 2 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C5 to C50 aryl group, or a substituted or unsubstituted carbon number 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 and a halogen group. selected,
* in Formula 2 represents a connection site with at least one of R1 to R10,
L1 is a direct bond, or a substituted or unsubstituted arylene group having 5 to 50 carbon atoms,
p is an integer from 1 to 5,
Ar is a substituted or unsubstituted aryl group having 5 to 30 carbon atoms. The method according to claim 1, wherein 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 A cyclic phenanthrenyl, or a substituted or unsubstituted triphenylenyl organic electroluminescent device. The organic electroluminescent device according to claim 1, wherein one of the hosts comprises a compound having a deuterium substitution rate of 10 to 100% of Formula 1. The organic electroluminescent device according to claim 1, wherein two of the hosts include a compound having a deuterium substitution rate of 10 to 100% of Formula 1. The organic electroluminescent device according to claim 1, wherein the mass ratio of the two types of the host is 1:9 to 9:1. The organic electroluminescent device according to claim 1, wherein the dipole moment (DM _host ) of the host of the emission layer is less than 0.5, respectively. The organic electroluminescent device according to claim 1, wherein the dipole moment of the first host (DM _host1 ) and the dipole moment of the second host (DM _host2 ) of the light emitting layer satisfy Equation 1:
[Equation 1]
|DM _host1 - DM _host2 | < 0.2 The organic electroluminescent device according to claim 1, wherein the organic electroluminescent device is of a multi-stack type, and one or two stacks of them include the two kinds of hosts. The organic electroluminescent device according to claim 1, wherein the emission spectrum of the emission layer including the two types of hosts and one type of dopant has λmax within 400 nm to 470 nm. The organic electroluminescent device according to claim 1, wherein the dopant is a fluorescent dopant. The organic electroluminescent device according to claim 1, wherein the dopant includes a pyrene-based compound. The organic electroluminescent device according to claim 1, wherein the dopant includes a non-pyrene-based compound. The organic electroluminescent device of claim 12, wherein the non-pyrene-based compound includes a boron-based compound. The organic electroluminescent device according to claim 1, wherein one of the two types of hosts is represented by a compound of Formula 3 below, and the other one is represented by a compound of Formula 4 below.
[Formula 3]

[Formula 4]

In Formulas 3 and 4, a, c, d and f are each an integer of 0 to 7, b and e are each an integer of 0 to 8, g is 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. The organic electroluminescent device according to claim 14, wherein L2 is phenylene unsubstituted or substituted with deuterium.

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