WO2021049840A1 - Heterocyclic compound and organic light-emitting device comprising same - Google Patents

Abstract

The present specification relates to a heterocyclic compound and an organic light-emitting device comprising same.

Description

Heterocyclic compound and organic light-emitting device comprising the same

This specification claims the benefit of the filing date of the Korean Patent Application No. 10-2019-0112880 filed with the Korean Intellectual Property Office on September 11, 2019, the entire contents of which are incorporated herein.

The present specification relates to a heterocyclic compound and an organic light emitting device including the same.

In general, the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy by using an organic material. An organic light emitting device using the organic light emitting phenomenon has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is often made of a multilayer structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device.For example, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of such an organic light emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. When it falls back to the ground, it glows.

Development of a new material for the organic light emitting device as described above is continuously required.

The present specification provides a heterocyclic compound and an organic light emitting device including the same.

The present specification provides a heterocyclic compound of Formula 1 below.

[Formula 1]

In Formula 1,

At least one of X1 to X3 is N, the rest are CH,

L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,

Ar2 and Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group,

Ar1 is a fluoranthenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, and a heterocyclic group; A fluorenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, and a heterocyclic group; Or containing at least one of O, N and S, and substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, alkyl groups, alkenyl groups, cycloalkyl groups, aryl groups, arylalkyl groups, arylalkenyl groups and heterocyclic groups It is a polycyclic heterocyclic group.

In addition, the present specification is a first electrode; A second electrode provided opposite to the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the above-described heterocyclic compound.

The organic light-emitting device using the heterocyclic compound according to an exemplary embodiment of the present specification may improve efficiency.

In the organic light-emitting device using the heterocyclic compound according to an exemplary embodiment of the present specification, a driving voltage may be lowered.

The organic light-emitting device using the heterocyclic compound according to an exemplary embodiment of the present specification may improve lifespan characteristics.

1 illustrates an organic light-emitting device 10 according to an exemplary embodiment of the present specification.

2 illustrates an organic light-emitting device 11 according to another exemplary embodiment of the present specification.

Hereinafter, the present specification will be described in detail.

The present specification provides a heterocyclic compound of Formula 1.

The heterocyclic compound according to an exemplary embodiment of the present specification is a structure in which a substituent is bonded to positions 1 and 5 of naphthalene, which is a substituent connecting an electron donor and an electron acceptor, through linking groups L1 and L2. By appropriately controlling the positions of separate electron donors and electron acceptors, the distribution and flow of electrons in the electron transport layer can be efficiently managed, maximizing the efficiency and life in the device.

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

In the present specification, when a member is said to be positioned "on" another member, this includes not only the case where the member is in contact with the other member, but also the case where another member exists between the two members.

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

The term "substituted" means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited as long as the position where the hydrogen atom is substituted, that is, the position where the substituent can be substituted, and when two or more are substituted , Two or more substituents may be the same or different from each other.

In the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; Nitrile group; Nitro group; Hydroxy 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 alkyl thioxy group; A substituted or unsubstituted arylthioxy group; A substituted or unsubstituted alkyl sulfoxy 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 a substituted or unsubstituted heterocyclic group substituted with one or two or more substituents selected from the group consisting of, or two or more of the substituents exemplified above are substituted with a connected substituent, or does not have any substituents. For example, "a substituent to which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent connected to two phenyl groups.

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, but are not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably 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 the number of carbon atoms of the alkoxy group is not particularly limited, it is preferably 1 to 30 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, 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, but is not limited thereto.

In the present specification, the amine group is -NH ₂ ; Alkylamine group; N-alkylarylamine group; Arylamine group; N-arylheteroarylamine 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 1 to 30. Specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 9-methyl-anthracenylamine group , Diphenylamine group, N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group; N-phenylnaphthylamine group; N-biphenylnaphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; N-biphenylphenanthrenylamine group; N-phenylfluorenylamine group; N-phenylterphenylamine group; N-phenanthrenylfluorenylamine group; N-biphenylfluorenylamine group, and the like, but are 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 heteroarylamine group are substituted with N of the amine group.

In the present specification, the alkyl group in the arylalkyl group, the alkylamine group, the N-arylalkylamine group, the alkylthioxy group, the alkylsulfoxy group, and the N-alkylheteroarylamine group is the same as the example of the aforementioned alkyl group. Specifically, the alkyl thioxy group includes methyl thioxy group, ethyl thioxy group, tert-butyl thioxy group, hexyl thioxy group, octyl thioxy group, and the like. And the like, but are 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, a stilbenyl group, and a styrenyl group, but are not limited thereto.

In the present specification, an arylalkenyl group means an alkenyl group substituted with an aryl group.

In the present specification, the silyl group is specifically trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited thereto.

In the present specification, the boron group _{may be -BR 100} R ₁₀₁ , the 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 C 1 to C 30 linear or branched alkyl group; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And 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 dinaphthylphosphine oxide, 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 it is preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, 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 has 10 to 30 carbon atoms. 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, and the like, but are limited thereto. no.

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

When the fluorenyl group is substituted,

,

,

,

And

Can be, etc. However, it is not limited thereto.

In the present specification, the "adjacent" group means a substituent substituted on an atom directly connected to the atom where the corresponding substituent is substituted, a substituent located three-dimensionally closest to the corresponding substituent, or another substituent substituted on the atom where the corresponding substituent is substituted. I can. For example, two substituents substituted at the ortho position in the benzene ring and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.

In the present specification, the aryl group in the arylalkyl group, arylalkenyl group, aryloxy group, arylthioxy group, arylsulfoxy group, N-arylalkylamine group, N-arylheteroarylamine group and arylphosphine group Same as the example. Specifically, the aryloxy group includes a phenoxy group, p-tolyloxy group, m-tolyloxy group, 3,5-dimethyl-phenoxy group, 2,4,6-trimethylphenoxy group, p-tert-butylphenoxy group, 3- Biphenyloxy 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, and 9-phenanthryloxy group, and the arylthioxy group is a phenylthioxy group, 2- There are a methylphenyl thioxy group, a 4-tert-butylphenyl thioxy group, and the like, and the aryl sulfoxy group includes a benzene sulfoxy group and a p-toluene sulfoxy group, but is not limited thereto.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine 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 is an atom other than carbon and includes one or more heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S. The number of carbon atoms is not particularly limited, but is preferably 2 to 30 carbon atoms, and the heterocyclic group may be monocyclic or polycyclic. Examples of the heterocyclic group include thiophene group, furanyl group, pyrrole group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, triazinyl group, tria Zolyl group, acridyl group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group , Isoquinolinyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzothiophene group, dibenzothiophene group, benzofuranyl group, p Nanthrolinyl group (phenanthroline), thiazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, phenoxazinyl group and dibenzofuranyl group, etc. It is not limited.

In the present specification, the heteroaryl group refers to an aromatic ring group among the heterocyclic groups.

In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine 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 those of the aforementioned heteroaryl group.

In the present specification, an arylene group means that the aryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aryl group described above may be applied.

According to an exemplary embodiment of the present specification, at least one of X1 to X3 is N, and the other is CH.

According to an exemplary embodiment of the present specification, any one of X1 to X3 is N, and the other is CH.

According to an exemplary embodiment of the present specification, two of X1 to X3 are N, and the other is CH.

According to an exemplary embodiment of the present specification, X1 to X3 are N.

According to an exemplary embodiment of the present specification, in Formula 1, L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group.

According to an exemplary embodiment of the present specification, in Formula 1, L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted C6 to C30 arylene group.

According to an exemplary embodiment of the present specification, in Formula 1, L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted C6 to C20 arylene group.

According to an exemplary embodiment of the present specification, in Formula 1, L1 and L2 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; Or a substituted or unsubstituted terphenylene group.

According to an exemplary embodiment of the present specification, in Formula 1, L1 and L2 are the same as or different from each other, and each independently a direct bond; A phenylene group unsubstituted or substituted with an alkyl group; A biphenylene group unsubstituted or substituted with an alkyl group; Or a terphenylene group unsubstituted or substituted with an alkyl group.

According to an exemplary embodiment of the present specification, Chemical Formula 1 is the following Chemical Formula 2.

[Formula 2]

In Formula 2, Ar1 to Ar3 and X1 to X3 are as defined in Formula 1,

R1 and R2 are the same as or different from each other, and each independently hydrogen or an alkyl group,

a1 and a2 are each an integer of 0 to 3.

According to an exemplary embodiment of the present specification, Chemical Formula 1 is any one of the following Chemical Formulas 3 to 7.

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

In Formulas 3 to 7, Ar1 to Ar3 and X1 to X3 are as defined in Formula 1,

R1 to R6 are the same as or different from each other, and each independently hydrogen or an alkyl group,

a1 and a2 are each an integer of 0 to 3,

a3 and a4 are each an integer of 0 to 2.

According to an exemplary embodiment of the present specification, in Formula 1, Ar2 and Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group.

According to an exemplary embodiment of the present specification, in Formula 1, Ar2 and Ar3 are the same as or different from each other, and each independently an aryl group.

According to an exemplary embodiment of the present specification, in Formula 1, Ar2 and Ar3 are the same as or different from each other, and each independently is an aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, in Formula 1, Ar2 and Ar3 are the same as or different from each other, and each independently is an aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, in Formula 1, Ar2 and Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group.

According to an exemplary embodiment of the present specification, in Formula 1, Ar2 and Ar3 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a substituent selected from the group consisting of an alkyl group, an aryl group, and a heterocyclic group; A biphenyl group unsubstituted or substituted with a substituent selected from the group consisting of an alkyl group, an aryl group, and a heterocyclic group; Or a naphthyl group unsubstituted or substituted with a substituent selected from the group consisting of an alkyl group, an aryl group, and a heterocyclic group.

According to an exemplary embodiment of the present specification, in Formula 1, Ar2 and Ar3 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a substituent selected from the group consisting of an alkyl group, a naphthyl group, and an N-containing heterocyclic group; A biphenyl group unsubstituted or substituted with a substituent selected from the group consisting of an alkyl group, a naphthyl group, and an N-containing heterocyclic group; Or a naphthyl group unsubstituted or substituted with a substituent selected from the group consisting of an alkyl group, a naphthyl group, and an N-containing heterocyclic group.

According to an exemplary embodiment of the present specification, in Formula 1, Ar2 and Ar3 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a substituent selected from the group consisting of an alkyl group, a naphthyl group, and a pyridine group; A biphenyl group unsubstituted or substituted with a substituent selected from the group consisting of an alkyl group, a naphthyl group, and a pyridine group; Or a naphthyl group unsubstituted or substituted with a substituent selected from the group consisting of an alkyl group, a naphthyl group, and a pyridine group.

According to an exemplary embodiment of the present specification, in Formula 1, Ar1 is substituted with one or more substituents selected from the group consisting of deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, and a heterocyclic group, or Unsubstituted fluoranthenyl group; A fluorenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, and a heterocyclic group; Including at least one of O, N and S, and unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, alkyl group, alkenyl group, cycloalkyl group, aryl group, arylalkyl group, arylalkenyl group and heterocyclic group It is a polycyclic heterocyclic group.

According to an exemplary embodiment of the present specification, in Formula 1, Ar1 is substituted with one or more substituents selected from the group consisting of deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, and a heterocyclic group, or It is an unsubstituted polycyclic aryl group.

According to an exemplary embodiment of the present specification, in Formula 1, Ar1 is substituted with one or more substituents selected from the group consisting of deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group and a heterocyclic group, or It is an unsubstituted bi- to 5-ring aryl group.

According to an exemplary embodiment of the present specification, in Formula 1, Ar1 is substituted with one or more substituents selected from the group consisting of deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group and a heterocyclic group, or It is an unsubstituted 3 to 4 ring aryl group.

According to an exemplary embodiment of the present specification, in Formula 1, Ar1 is substituted with one or more substituents selected from the group consisting of deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group and a heterocyclic group, or It is an unsubstituted fluorenyl group.

According to an exemplary embodiment of the present specification, in Formula 1, Ar1 is a fluorenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group and an aryl group.

According to an exemplary embodiment of the present specification, in Formula 1, Ar1 is a fluorenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of a methyl group and a phenyl group.

According to an exemplary embodiment of the present specification, in Formula 1, Ar1 is substituted with one or more substituents selected from the group consisting of deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, and a heterocyclic group, or It is an unsubstituted fluoranthenyl group.

According to an exemplary embodiment of the present specification, in Chemical Formula 1, Ar1 is a fluoranthenyl group.

According to an exemplary embodiment of the present specification, in Formula 1, Ar1 includes at least one of O, N and S, and deuterium, alkyl group, alkenyl group, cycloalkyl group, aryl group, arylalkyl group, arylalkenyl group, and hetero It is a polycyclic heterocyclic group unsubstituted or substituted with one or more substituents selected from the group consisting of a cyclic group.

According to an exemplary embodiment of the present specification, in Formula 1, Ar1 includes at least one of O, N and S, and deuterium, alkyl group, alkenyl group, cycloalkyl group, aryl group, arylalkyl group, arylalkenyl group, and hetero It is a bicyclic to tricyclic heterocyclic group unsubstituted or substituted with one or more substituents selected from the group consisting of a cyclic group.

According to an exemplary embodiment of the present specification, in Formula 1, Ar1 is substituted with one or more substituents selected from the group consisting of deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, and a heterocyclic group, or It is an unsubstituted benzoimidazolyl group.

According to an exemplary embodiment of the present specification, in Formula 1, Ar1 is a benzoimidazolyl group unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group, an aryl group, and a heterocyclic group.

According to an exemplary embodiment of the present specification, in Formula 1, Ar1 is a benzoimidazolyl group unsubstituted or substituted with one or more substituents selected from the group consisting of a methyl group, an ethyl group, a phenyl group, and a pyridyl group.

According to an exemplary embodiment of the present specification, in Formula 1, Ar1 is substituted with one or more substituents selected from the group consisting of deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, and a heterocyclic group, or It is an unsubstituted benzotriazolyl group.

According to an exemplary embodiment of the present specification, in Formula 1, Ar1 is substituted with one or more substituents selected from the group consisting of deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, and a heterocyclic group, or It is an unsubstituted benzothiazolyl group.

According to an exemplary embodiment of the present specification, in Formula 1, Ar1 is substituted with one or more substituents selected from the group consisting of deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, and a heterocyclic group, or It is an unsubstituted benzoxazolyl group.

According to an exemplary embodiment of the present specification, in Formula 1, Ar1 is substituted with one or more substituents selected from the group consisting of deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, and a heterocyclic group, or It is an unsubstituted carbazolyl group.

According to an exemplary embodiment of the present specification, in Formula 1, Ar1 is a benzotriazolyl group; Benzothiazolyl group; Benzoxazolyl group; Or a carbazolyl group.

According to an exemplary embodiment of the present specification, Formula 1 is selected from the following compounds.

.

According to an exemplary embodiment of the present specification, the first electrode; A second electrode provided opposite to the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the aforementioned heterocyclic compound.

According to an exemplary embodiment of the present specification, the organic material layer of the organic light emitting device of the present specification may be formed in a single-layer structure, but may be formed in a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, an electron suppression layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and the like as an organic material layer. However, the structure of the organic light-emitting device is not limited thereto, and may include fewer or more organic layers.

The organic light-emitting device may have, for example, a stacked structure as described below, but is not limited thereto.

(1) Anode/Hole Transport Layer/Light-Emitting Layer/Anode

(2) Anode/Hole Injection Layer/Hole Transport Layer/Light-Emitting Layer/Anode

(3) Anode/Hole Injection Layer/Hole Buffer Layer/Hole Transport Layer/Light-Emitting Layer/Anode

(4) Anode/hole transport layer/light-emitting layer/electron transport layer/cathode

(5) Anode/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode

(6) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/cathode

(7) Anode/hole injection layer/hole transport layer/light-emitting layer/electron transport layer/electron injection layer/cathode

(8) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/cathode

(9) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode

(10) Anode/hole transport layer/electron suppression layer/light-emitting layer/electron transport layer/cathode

(11) Anode/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/electron injection layer/cathode

(12) Anode/hole injection layer/hole transport layer/electron suppression layer/light-emitting layer/electron transport layer/cathode

(13) Anode/hole injection layer/hole transport layer/electron suppression layer/light-emitting layer/electron transport layer/electron injection layer/cathode

(14) Anode/Hole transport layer/Light-emitting layer/Hole blocking layer/Electron transport layer/Anode

(15) Anode/Hole transport layer/Light emitting layer/Hole blocking layer/Electron transport layer/Electron injection layer/Anode

(16) Anode/hole injection layer/hole transport layer/light-emitting layer/hole blocking layer/electron transport layer/cathode

(17) Anode/Hole injection layer/Hole transport layer/Light emitting layer/Hole blocking layer/Electron transport layer/Electron injection layer/Anode

(18) Anode/hole injection layer/hole transport layer/light-emitting layer/layer that simultaneously injects and transports electrons/cathode

(19) Anode/Hole injection layer/Hole transport layer/Electron suppression layer/Light-emitting layer/Hole blocking layer/Electron transport layer/Electron injection layer/Anode

(20) Anode/hole injection layer/hole transport layer/electron suppression layer/light-emitting layer/hole blocking layer/electron transport layer/cathode

(21) Anode/Hole Injection Layer/Hole Transport Layer/Electron Suppression Layer/Light-Emitting Layer/Hole Blocking Layer/Layer for Simultaneous Electron Injection and Transport/Anode

For example, the structure of the organic light-emitting device of the present specification may have a structure as shown in FIGS. 1 and 2, but is not limited thereto.

1 illustrates a structure of an organic light-emitting device 10 in which a first electrode 30, a light emitting layer 40, and a second electrode 50 are sequentially stacked on a substrate 20. 1 is an exemplary structure of an organic light emitting device according to an exemplary embodiment of the present specification, and may further include another organic material layer.

2, a first electrode 30, a hole injection layer 60, a hole transport layer 70, a light emitting layer 40, an electron transport layer 80, an electron injection layer 90, and a second electrode ( 50) is an example of a structure of an organic light-emitting device stacked sequentially. 2 is an exemplary structure according to the exemplary embodiment of the present specification, and may further include another organic material layer.

According to an exemplary embodiment of the present specification, the organic material layer includes an electron injection layer, and the electron injection layer includes the heterocyclic compound of Formula 1 above.

According to an exemplary embodiment of the present specification, the organic material layer includes an electron transport layer, and the electron transport layer includes the heterocyclic compound of Formula 1 above.

According to an exemplary embodiment of the present specification, the organic material layer includes a layer that simultaneously injects and transports electrons, and the layer that simultaneously injects and transports electrons includes the heterocyclic compound of Formula 1 above.

A hole control layer or an electron suppression layer may be provided between the hole transport layer and the light emitting layer. The hole control layer or the electron suppression layer may be formed of the above-described compound or a material known in the art.

According to an exemplary embodiment of the present specification, the organic material layer includes an electron inhibiting layer, and the electron inhibiting layer includes the heterocyclic compound of Formula 1 above.

An electron controlling layer or a hole blocking layer may be provided between the electron transport layer and the light emitting layer. The electron controlling layer or the hole blocking layer may be formed of the above-described compound or a material known in the art.

According to an exemplary embodiment of the present specification, the organic material layer includes a hole blocking layer, and the hole blocking layer includes the heterocyclic compound of Formula 1 above.

According to an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes the heterocyclic compound of Formula 1 as a host of the emission layer.

In the exemplary embodiment of the present specification, the organic material layer may include the heterocyclic compound of Formula 1 as a host, and may include other organic compounds, metals, or metal compounds as a dopant.

The dopant may be one or more selected from the compounds exemplified below, but is not limited thereto.

According to an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes a compound of Formula 1-A below.

[Formula 1-A]

In Formula 1-A,

n1 is an integer greater than or equal to 1,

Ar7 is a substituted or unsubstituted monovalent or higher benzofluorene group; A substituted or unsubstituted monovalent or more fluoranthene group; A substituted or unsubstituted monovalent or higher pyrene group; Or a substituted or unsubstituted monovalent or higher chrysene group,

L4 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Ar8 and Ar9 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted arylalkyl group; Or a substituted or unsubstituted heterocyclic group, or may be bonded to each other to form a substituted or unsubstituted ring,

When n1 is 2 or more, the structures in parentheses of 2 or more are the same as or different from each other.

According to an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes the compound of Formula 1-A as a dopant of the emission layer.

According to an exemplary embodiment of the present specification, L4 is a direct bond.

According to an exemplary embodiment of the present specification, n1 is 2.

In the exemplary embodiment of the present specification, Ar7 is a divalent pyrene group unsubstituted or substituted with deuterium, methyl group, ethyl group, isopropyl group, or tert-butyl group; Or a divalent chrysene group unsubstituted or substituted with a deuterium, methyl group, ethyl group, or tert-butyl group.

According to the exemplary embodiment of the present specification, Ar8 and Ar9 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to the exemplary embodiment of the present specification, Ar8 and Ar9 are the same as or different from each other, and each independently a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a nitrile group, or an unsubstituted silyl group substituted with an alkyl group. It is an aryl group.

According to an exemplary embodiment of the present specification, Ar8 and Ar9 are the same as or different from each other, and are each independently an aryl group unsubstituted or substituted with a silyl group substituted with an alkyl group.

According to an exemplary embodiment of the present specification, Ar8 and Ar9 are the same as or different from each other, and are each independently an aryl group unsubstituted or substituted with a trimethylsilyl group.

According to an exemplary embodiment of the present specification, Ar8 and Ar9 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted terphenyl group.

According to an exemplary embodiment of the present specification, Ar8 and Ar9 are the same as or different from each other, and each independently a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a nitrile group, or a phenyl group unsubstituted or substituted with a trimethylsilyl group.

According to the exemplary embodiment of the present specification, Ar8 and Ar9 are the same as or different from each other, and each independently a methyl group, an ethyl group, a tert-butyl group, a nitrile group, or a biphenyl group unsubstituted or substituted with a trimethylsilyl group.

According to the exemplary embodiment of the present specification, Ar8 and Ar9 are the same as or different from each other, and each independently a methyl group, an ethyl group, a tert-butyl group, a nitrile group, or a terphenyl group unsubstituted or substituted with a trimethylsilyl group.

According to the exemplary embodiment of the present specification, Ar8 and Ar9 are the same as or different from each other, and each independently a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar8 and Ar9 are the same as or different from each other, and each independently a methyl group, an ethyl group, a tert-butyl group, a nitrile group, a silyl group substituted with an alkyl group, or a phenyl group substituted or unsubstituted hetero It is a ring group.

According to an exemplary embodiment of the present specification, Ar8 and Ar9 are the same as or different from each other, and each independently a methyl group, an ethyl group, a tert-butyl group, a nitrile group, a trimethylsilyl group, or a dibenzofuran group unsubstituted or substituted with a phenyl group. to be.

According to an exemplary embodiment of the present specification, Formula 1-A is selected from the following compounds.

According to an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes a compound represented by Formula 2-A below.

[Formula 2-A]

In Formula 2-A,

Ar11 and Ar12 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic aryl group; Or a substituted or unsubstituted polycyclic aryl group,

G1 to G8 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted monocyclic aryl group; Or a substituted or unsubstituted polycyclic aryl group.

According to an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes the compound of Formula 2-A as a host of the emission layer.

According to the exemplary embodiment of the present specification, Ar11 and Ar12 are the same as or different from each other, and each independently a substituted or unsubstituted polycyclic aryl group.

According to the exemplary embodiment of the present specification, Ar11 and Ar12 are the same as or different from each other, and are each independently a substituted or unsubstituted polycyclic aryl group having 10 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar11 and Ar12 are the same as or different from each other, and each independently a substituted or unsubstituted naphthyl group.

According to an exemplary embodiment of the present specification, Ar11 and Ar12 are the same as or different from each other, and each independently a substituted or unsubstituted 1-naphthyl group.

According to an exemplary embodiment of the present specification, Ar11 and Ar12 are 1-naphthyl groups.

According to an exemplary embodiment of the present specification, G1 to G8 are hydrogen.

According to an exemplary embodiment of the present specification, Formula 2-A is the following compound.

According to an exemplary embodiment of the present specification, the organic material layer includes an emission layer, the emission layer includes the compound of Formula 1-A as a dopant of the emission layer, and the compound of Formula 2-A as a host of the emission layer.

According to the exemplary embodiment of the present specification, the organic material layer may further include one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

The organic light-emitting device of the present specification may be manufactured by materials and methods known in the art, except that at least one of the organic material layers includes the heterocyclic compound of the present specification, that is, the heterocyclic compound of Formula 1. .

When the organic light-emitting 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 light emitting device of the present specification may be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation, a metal or a conductive metal oxide or an alloy thereof is deposited on the substrate. It can be manufactured by forming a first electrode, forming an organic material layer including a hole injection layer, a hole transport layer, an emission layer, and an electron transport layer thereon, and then depositing a material that can be used as a second electrode thereon. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a second electrode material, an organic material layer, and a first electrode material on a substrate. In addition, the heterocyclic compound of Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, ink jet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.

According to an exemplary embodiment of the present specification, the first electrode is an anode, and the second electrode is a cathode.

According to another exemplary embodiment of the present specification, the first electrode is a cathode, and the second electrode is an anode.

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, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of a metal and an oxide such as ZnO:Al or SnO _{2 :Sb;} Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.

It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; There are a multilayered material such as LiF/Al, LiO ₂ /Al, and Mg/Ag, but are not limited thereto.

The hole injection layer is a layer that injects holes from an electrode as a hole injection material, and has an ability to transport holes as a hole injection material, so that it has a hole injection effect at the anode, an excellent hole injection effect for a light emitting layer or a light emitting material. , A compound that prevents the movement of excitons generated in the light-emitting layer to the electron injection layer or the electron injection material and has excellent thin film formation ability is preferable. It is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. Organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the emission layer.The hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the emission layer, and has high mobility for holes. The material is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer including a conjugated portion and a non-conjugated portion, but are not limited thereto.

The electron suppression layer is a layer capable of improving the life and efficiency of the device by preventing electrons injected from the electron injection layer from entering the hole injection layer through the light emitting layer. It may be formed in an appropriate portion between the injection layer.

As the light-emitting material of the light-emitting layer, a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency against fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzothiazole, and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

The emission layer may include a host material and a dopant material. The host material includes a condensed aromatic ring derivative or a hetero ring-containing compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Examples of the dopant material include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, periflanthene and the like having an arylamino group, and the styrylamine compound is substituted or unsubstituted As a compound in which at least one arylvinyl group is substituted on the arylamine, one or two or more substituents selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group and arylamino group are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, and styryltetraamine, but are not limited thereto. In addition, examples of the metal complex include, but are not limited to, an iridium complex and a platinum complex.

The hole blocking layer is a layer capable of improving the life and efficiency of the device by preventing holes injected from the hole injection layer from entering the electron injection layer through the emission layer. It may be formed in an appropriate portion between the injection layer.

The electron transport material of the electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the emission layer. The electron transport material is a material that can receive electrons from the cathode and transfer them to the emission layer. This large material is suitable. The electron transport material of the electron transport layer may include the compound of Formula 1, and a layer may be formed alone or a layer may be formed with an additional electron transport material. When the electron transport layer is formed of multiple layers, at least one electron transport layer may include the compound of Formula 1, and the remaining electron transport layer may be formed of a known electron transport material. Specific examples of the electron transport material include an 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 transport layer can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials that have a low work function and are followed by an aluminum layer or a silver layer. Specifically, they are cesium, barium, calcium, ytterbium, and samarium, and in each case an aluminum layer or a silver layer follows.

The electron injection layer is a layer that injects electrons from the electrode, 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, and injects holes of excitons generated from the light emitting layer. A compound that prevents migration to the layer and is excellent in thin film forming ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. Complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

Examples of the metal complex compound include lithium 8-hydroxyquinolinato, 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-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc. It is not limited to this.

The organic light-emitting device according to the present specification may be a top emission type, a bottom emission type, or a double-sided emission type depending on the material used.

According to the exemplary embodiment of the present specification, the heterocyclic compound of Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.

Hereinafter, examples will be described in detail in order to describe the present specification in detail. However, the embodiments according to the present specification may be modified in various forms, and the scope of the present specification is not construed as being limited to the embodiments described below. The embodiments of the present specification are provided to more completely describe the present specification to those of ordinary skill in the art.

[Preparation Example 1] Synthesis of Chemical Formula E1

The compound 2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(3-(5-(4,4,5,5-tetramethyl-1,3,2- Dioxaborolan-2-yl)naphthalen-1-yl)phenyl)-1,3,5-triazine (10.0g, 15.7mmol) and 1-(4-bromophenyl)-2-ethyl-1H-benzo [d]imidazole (5.0g, 16.6mmol) was completely dissolved in tetrahydrofuran (100ml), potassium carbonate (7.4g, 53.7mmol) was dissolved in 100ml of water and added, tetrakistriphenyl-phosphine palladium ( 620mg, 0.537mmol) was added, followed by heating and stirring for 4 hours. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate solution was removed to filter the white solid. The filtered white solid was washed twice with tetrahydrofuran and ethyl acetate, respectively, to prepare a compound of Formula E1 (9.5g, yield 82%).

MS[M+H] ⁺ = 732

[Preparation Example 2] Synthesis of Chemical Formula E2

In Preparation Example 1, 2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(3-(5-(4,4,5,5-tetramethyl-1,3) ,2-dioxaborolan-2-yl)naphthalen-1-yl)phenyl)-1,3,5-triazine instead of 9-(4-(5-(3-(4,4,5,5-tetra) Using methyl-1,3,2-dioxaborolan-2-yl)phenyl)naphthalen-1-yl)phenyl)-9H-carbazole, and 1-(4-bromophenyl)-2-ethyl-1H -Preparation above, except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine was used instead of benzo[d]imidazole In the same manner as in Example 1, the compound of Formula E2 was prepared.

MS[M+H] ⁺ = 753

[Preparation Example 3] Synthesis of Chemical Formula E3

In Preparation Example 1, 2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(3-(5-(4,4,5,5-tetramethyl-1,3) ,2-dioxaborolan-2-yl)naphthalen-1-yl)phenyl)-1,3,5-triazine instead of (5-(4-(4,6-diphenyl-1,3,5-tri Azin-2-yl)phenyl)naphthalen-1-yl)boronic acid is used, and 3-bromofloran is used instead of 1-(4-bromophenyl)-2-ethyl-1H-benzo[d]imidazole Except for using tin, the compound of Formula E3 was prepared in the same manner as in Preparation Example 1.

MS[M+H] ⁺ = 635

[Preparation Example 4] Synthesis of Chemical Formula E4

In Preparation Example 1, 2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(3-(5-(4,4,5,5-tetramethyl-1,3) ,2-dioxaborolan-2-yl)naphthalen-1-yl)phenyl)-1,3,5-triazine instead of (4-(5-(4-(4,6-diphenyl-1,3, 5-triazine-2-yl)phenyl)naphthalen-1-yl)phenyl)boronic acid is used, and 1-(4-bromophenyl)-2-ethyl-1H-benzo[d]imidazole is replaced with 2 -A compound of Formula E4 was prepared in the same manner as in Preparation Example 1, except that bromo-9,9-dimethyl-9H-fluorene was used.

MS[M+H] ⁺ = 703

[Preparation Example 5] Synthesis of Chemical Formula E5

In Preparation Example 1, 2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(3-(5-(4,4,5,5-tetramethyl-1,3) 2,4-diphenyl-6-(4-(4-(4,4,5) instead of ,2-dioxaborolan-2-yl)naphthalen-1-yl)phenyl)-1,3,5-triazine ,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-1-yl)phenyl)-1,3,5-triazine, 1-(4-bromophenyl)-2- The compound of Formula E5 was prepared in the same manner as in Preparation Example 1, except that 2-(4-bromophenyl)benzo[d]oxazole was used instead of ethyl-1H-benzo[d]imidazole.

MS[M+H] ⁺ = 628

[Preparation Example 6] Synthesis of Chemical Formula E6

In Preparation Example 5, in the same manner as in Preparation Example 5, except that 2-(4-bromophenyl)benzo[d]cyazole was used instead of 2-(4-bromophenyl)benzo[d]oxazole. The compound of Formula E6 was prepared.

MS[M+H] ⁺ = 644

Example 1

A glass substrate coated with a thin film of ITO (indium tin oxide) having a thickness of 1,000Å was put in distilled water dissolved in a detergent and washed with ultrasonic waves. At this time, a product made by Fischer Co. was used as a detergent, and distilled water secondarily filtered with a filter manufactured by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, it was repeated twice with distilled water to perform ultrasonic cleaning for 10 minutes. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

A hole injection layer was formed by thermally vacuum evaporating a compound of the following compound HI1 and the following compound HI2 to a thickness of 100 Å in a ratio of 98:2 (molar ratio) on an ITO transparent electrode, which is an anode thus prepared. A hole transport layer was formed by vacuum depositing a compound of Formula HT1 to a thickness of 1150 Å on the hole injection layer. Subsequently, an electron suppressing layer was formed by vacuum depositing a compound of EB1 with a film thickness of 50 Å on the hole transport layer. Subsequently, a light emitting layer was formed by vacuum depositing a compound of the following formula BH and a compound of the following formula BD with a film thickness of 200 Å on the electron inhibiting layer at a weight ratio of 50:1. A hole blocking layer was formed by vacuum depositing a compound of Formula HB1 with a film thickness of 50 Å on the emission layer. Subsequently, on the hole blocking layer, the compound E1 synthesized in Preparation Example 1 and the compound of the following formula LiQ were vacuum-deposited at a weight ratio of 1:1 to form an electron transport layer with a thickness of 30Å. Lithium fluoride (LiF) in a thickness of 12 Å and aluminum in a thickness of 1,000 Å were sequentially deposited on the electron transport layer to form a negative electrode.

In the above process, the deposition rate of the organic material was maintained at 0.4 ~ 0.7Å/sec, the deposition rate of lithium fluoride at the negative electrode was 0.3Å/sec, and the deposition rate of aluminum was 2Å/sec, and the vacuum degree during deposition was 2×10 ^{− Maintaining 7} ~ 5 × 10 ^-6 torr, an organic light emitting device was manufactured.

Examples 2 to 6

An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compound shown in Table 1 was used instead of the compound E1 of Example 1.

Comparative Examples 1 to 9

An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compound shown in Table 1 was used instead of the compound E1 of Example 1. The compounds of ET2 to ET10 used in Table 1 are as follows.

When a current was applied to the organic light emitting devices fabricated in Examples 1 to 6 and Comparative Examples 1 to 9, voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in Table 1 below. T ₉₅ refers to the time it takes for the luminance to decrease from the initial luminance (1600 nits) to 95%.

	Compound (electron transport layer)	Voltage(V)(@20mA/cm 2 )	Efficiency (cd/A)(@20mA/cm 2 )	Color coordinate (x,y)	T 95 (hr)
Example 1	Compound E1	4.15	6.21	(0.142, 0.044)	223
Example 2	Compound E2	4.25	6.42	(0.143, 0.045)	241
Example 3	Compound E3	4.22	6.16	(0.143, 0.046)	268
Example 4	Compound E4	4.18	6.43	(0.143, 0.044)	235
Example 5	Compound E5	4.14	6.32	(0.143, 0.044)	245
Example 6	Compound E6	4.21	6.13	(0.142, 0.044)	233
Comparative Example 1	ET 2	4.34	5.72	(0.145, 0.046)	167
Comparative Example 2	ET 3	5.67	5.83	(0.144, 0.044)	61
Comparative Example 3	ET 4	4.53	5.55	(0.144, 0.047)	86
Comparative Example 4	ET 5	5.21	5.52	(0.143, 0.046)	146
Comparative Example 5	ET 6	6.46	5.31	(0.142, 0.045)	77
Comparative Example 6	ET 7	5.74	5.79	(0.143, 0.044)	138
Comparative Example 7	ET 8	5.91	5.44	(0.143, 0.045)	126
Comparative Example 8	ET 9	6.08	5.97	(0.144, 0.045)	86
Comparative Example 9	ET 10	5.88	5.85	(0.143, 0.043)	92

As shown in Table 1, in the case of an organic light-emitting device manufactured using the compound of the present invention as an electron transport layer, the organic light-emitting device exhibits excellent characteristics in terms of efficiency, driving voltage and/or stability.

The organic light emitting devices of Examples 1 to 6 have lower voltage than the organic light emitting devices manufactured using Comparative Examples 1 to 3 using compounds ET2 to ET4, which are compounds having substituents at positions 1 and 4 of the naphthalene core, as electron transport layers, respectively. It exhibited the characteristics of high efficiency and long life.

In addition, having a substituent at positions 1 and 5 of the naphthalene core, ET5 and ET6 which are pyridine derivatives as substituents of Ar1, ET7 which is a phenyl group substituted with a cyano group, ET8 which is a triphenylenyl group, ET9 which is a pyrimidine derivative, and a triazine derivative. Compared to organic light-emitting devices manufactured using phosphorus ET10 as an electron transport layer, respectively, the organic light-emitting devices of Examples 1 to 6 exhibited characteristics of low voltage, high efficiency, and long lifespan.

Although the preferred embodiment (electron transport layer) of the present invention has been described above, the present invention is not limited thereto, and various modifications can be made within the scope of the claims and the detailed description of the invention. Belongs to the category of.

Claims (11)

1. Heterocyclic compounds of the following formula (1):

   [Formula 1]

   

   In Formula 1,

   At least one of X1 to X3 is N, the rest are CH,

   L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,

   Ar2 and Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group,

   Ar1 is a fluoranthenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, and a heterocyclic group; A fluorenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, and a heterocyclic group; Or containing at least one of O, N and S, and substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, alkyl groups, alkenyl groups, cycloalkyl groups, aryl groups, arylalkyl groups, arylalkenyl groups and heterocyclic groups It is a polycyclic heterocyclic group.
2. The method according to claim 1, wherein Ar2 and Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group that will be a heterocyclic compound.
3. The method according to claim 1, wherein L1 and L2 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; Or a substituted or unsubstituted terphenylene group that will be a heterocyclic compound.
4. The method according to claim 1, Ar1 is a fluorenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group and a heterocyclic group; A fluoranthenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, and a heterocyclic group; A benzoimidazolyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, and a heterocyclic group; A benzotriazolyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, and a heterocyclic group; A benzothiazolyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, and a heterocyclic group; A benzoxazolyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, and a heterocyclic group; Or a heterocyclic compound that is a carbazolyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, and a heterocyclic group.
5. The heterocyclic compound of claim 1, wherein Formula 1 is the following Formula 2:

   [Formula 2]

   

   In Formula 2, Ar1 to Ar3 and X1 to X3 are as defined in Formula 1,

   R1 and R2 are the same as or different from each other, and each independently hydrogen or an alkyl group,

   a1 and a2 are each an integer of 0 to 3.
6. The heterocyclic compound according to claim 1, wherein Formula 1 is any one of the following Formulas 3 to 7:

   [Formula 3]

   

   [Formula 4]

   

   [Formula 5]

   

   [Formula 6]

   

   [Formula 7]

   

   In Formulas 3 to 7, Ar1 to Ar3 and X1 to X3 are as defined in Formula 1,

   R1 to R6 are the same as or different from each other, and each independently hydrogen or an alkyl group,

   a1 and a2 are each an integer of 0 to 3,

   a3 and a4 are each an integer of 0 to 2.
7. The heterocyclic compound of claim 1, wherein Formula 1 is selected from the following compounds:

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   .
8. A first electrode; A second electrode provided opposite to the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises the heterocyclic compound of any one of claims 1 to 7 device.
9. The method according to claim 8, wherein the organic material layer includes an electron injection layer, an electron transport layer, or a layer for simultaneously injecting and transporting electrons, and the layer for simultaneously injecting and transporting electrons, the electron injection layer, the electron transport layer, or the heterocyclic compound The organic light-emitting device comprising a.
10. The organic light-emitting device of claim 8, wherein the organic material layer includes a hole blocking layer, and the hole blocking layer includes the heterocyclic compound.
11. The organic light-emitting device of claim 8, wherein the organic material layer includes an emission layer, and the emission layer includes the heterocyclic compound as a host of the emission layer.

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