KR20220136712A - Compound and organic light emitting device comprising same - Google Patents

Abstract

The present specification provides a compound represented by a chemical formula 1 and an organic light emitting device including the same. The compound according to at least one exemplary embodiment of the present specification may improve efficiency and/or lifetime characteristics and alleviate low driving voltage in the organic light emitting device.

Description

Compound and organic light emitting device comprising the same

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

In general, the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic material layer therebetween. Here, the organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. When a voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer from the anode and electrons from the cathode are injected into the organic material layer. When the injected holes and electrons meet, excitons are formed, and the excitons It lights up when it falls back to the ground state.

The development of new materials for the organic light emitting device as described above is continuously required.

International Patent Publication No. 2016-032137

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

An exemplary embodiment of the present specification provides a compound represented by the following formula (1).

[Formula 1]

In Formula 1,

Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

L1 to L6 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,

At least one of L5 and L6 is an arylene group consisting of a substituted or unsubstituted monocyclic ring; Or a substituted or unsubstituted tricyclic or more arylene group,

a and b are each an integer of 0 to 3, and when a and b are each 2 or more, L5 and L6 are each the same as or different from each other,

a+b is greater than or equal to 1.

In addition, one embodiment of the present specification is an anode; cathode; and at least one organic material layer provided between the anode and the cathode, wherein at least one of the organic material layers includes the compound represented by Formula 1 above.

The compound described herein may be used as a material for an organic material layer of an organic light emitting device. The compound according to at least one embodiment of the present specification may improve efficiency, low driving voltage, and/or lifespan characteristics in an organic light emitting device. In particular, the compounds described herein can be used as hole injection, hole transport, hole injection and hole transport, electron blocking, luminescence, hole blocking, electron transport, or electron injection material. In addition, compared to the conventional organic light emitting device, there is an effect of a low driving voltage, high efficiency, and/or a long lifespan.

1 shows an example of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 6, and a cathode 10 are sequentially stacked.
2 is a substrate (1), anode (2), hole injection layer (3), hole transport layer (4), electron blocking layer (5), light emitting layer (6), hole blocking layer (7), electron transport layer (8) , an example of an organic light emitting device in which the electron injection layer 9 and the cathode 10 are sequentially stacked.
3 shows a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, a hole blocking layer 7, an electron transport and injection layer An example of an organic light emitting device in which (11) and the cathode (10) are sequentially stacked is shown.

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

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, when a member is said to be located "on" another member, this includes not only a case in which a member is in contact with another member but also a case in which another member exists between the two members.

" 또는 점선은 화학식 또는 화합물에 결합되는 위치를 의미한다.In this specification, "

" or the dotted line means the position bonded to the formula or compound.

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 in which 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 (-CN); nitro group; hydroxyl group; an alkyl group; cycloalkyl group; alkoxy group; phosphine oxide group; aryloxy group; alkyl thiooxy group; arylthioxy group; an alkyl sulfoxy group; arylsulfoxy group; alkenyl group; silyl group; boron group; amine group; aryl group; Or it means that it is substituted with one or more substituents selected from the group consisting of a heterocyclic group, or 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 in 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 in which two phenyl groups are connected.

As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group; nitrile group; nitro group; hydroxyl group; amino group; silyl group; boron group; alkoxy group; aryloxy group; an alkyl group; cycloalkyl group; aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a 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.

As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group; nitrile group; an alkyl group; aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a 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.

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

In the present specification, examples of the halogen group include fluorine (-F), chlorine (-Cl), bromine (-Br) or iodine (-I).

In the present specification, the silyl group may be represented by the formula of -SiY _a Y _b Y _c , wherein Y _a , Y _b and Y _c are each hydrogen; a substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The silyl group specifically includes, but is not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like. does not

In the present specification, the boron group may be represented by the formula of -BY _d Y _e , wherein Y _d and Y _e are each hydrogen; a substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. Specifically, the boron group includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group, and the like.

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 60. According to an exemplary embodiment, the number of carbon atoms in the alkyl group is 1 to 30. According to another exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, pentyl group, n-pentyl group, hexyl group, n -hexyl group, heptyl group, n-heptyl group, octyl group, n-octyl group, etc., but are not limited thereto.

In the present specification, the description of the above-described alkyl group may be applied except that the arylalkyl group is substituted with an aryl group.

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-C20. 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, and the like, but is not limited thereto.

The substituents containing an alkyl group, an alkoxy group, and other alkyl group moieties described herein include both straight-chain or pulverized forms.

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 40. According to an exemplary embodiment, the carbon number of the alkenyl group is 2 to 20. According to another exemplary embodiment, the carbon number of the alkenyl group is 2 to 10. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. 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, styrenyl group, and the like, but are not limited thereto.

In the present specification, the alkynyl group is a substituent including a triple bond between a carbon atom and a carbon atom, and may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the carbon number of the alkynyl group is 2 to 20. According to another exemplary embodiment, the carbon number of the alkynyl group is 2 to 10.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like, but is not limited thereto.

In the present specification, the amine group is —NH ₂ , and the amine group may be substituted with the aforementioned alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, and combinations thereof. The number of carbon atoms of the substituted amine group is not particularly limited, but is preferably 1 to 30. According to an exemplary embodiment, the carbon number of the amine group is 1 to 20. According to an exemplary embodiment, the carbon number of the amine group is 1 to 10. Specific examples of the substituted amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a 9,9-dimethylfluorenylphenylamine group, a pyridylphenylamine group, and a diphenylamine group. group, phenylpyridylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, dibenzofuranylphenylamine group, 9-methylanthracenylamine group, diphenylamine group, phenylnaphthylamine group, There is a ditolylamine group, a phenyltolylamine group, a diphenylamine 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 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 30. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 20. The aryl group may be a monocyclic aryl group, such as a phenyl group, a biphenyl group, a terphenyl group, or a quaterphenyl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a triphenylenyl group, a chrysenyl group, a fluorenyl group, a triphenylenyl group, etc., but is limited thereto. it's not going to be

In the present specification, the aryl group may be a monocyclic aryl group or a polycyclic aryl group (an aryl group having two or more rings). A monocyclic aryl group is a phenyl group; Or it may mean a group in which two or more phenyl groups are connected. The monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, and the like, but is not limited thereto. The polycyclic aryl group may refer to a group in which two or more monocyclic rings are condensed, such as a naphthyl group or a phenanthrenyl group. The polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a triphenyl group, a chrysenyl group, a fluorenyl group, a triphenylenyl group, etc., but is not limited thereto. .

In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. In this case, the spiro structure may be an aromatic hydrocarbon ring or an aliphatic hydrocarbon ring.

,

,

등의 스피로플루오레닐기,

(9,9-디메틸플루오레닐기), 및

(9,9-디페닐플루오레닐기) 등의 치환된 플루오레닐기가 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

,

spirofluorenyl groups such as

(9,9-dimethyl fluorenyl group), and

It may be a substituted fluorenyl group such as (9,9-diphenylfluorenyl group). However, the present invention is not limited thereto.

In the present specification, the description of the above-described aryl group may be applied to the aryl group in the aryloxy group.

In the present specification, the description of the above-described alkyl group may be applied to the alkyl group in the alkyl thiooxy group and the alkyl sulfoxy group.

In the present specification, the description of the above-described aryl group may be applied to the aryl group in the arylthioxy group and the arylsulfoxy group.

In the present specification, the heterocyclic group is a cyclic group including at least one of N, O, P, S, Si and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but it is preferably from 2 to 60 carbon atoms. According to an exemplary embodiment, the heterocyclic group has 2 to 30 carbon atoms. According to an exemplary embodiment, the heterocyclic group has 2 to 20 carbon atoms. Examples of the heterocyclic group include a pyridine group, a pyrrole group, a pyrimidine group, a quinoline group, a pyridazinyl group, a furan group, a thiophene group, an imidazole group, a pyrazole group, a dibenzofuran group, a dibenzothiophene group, and a carba group. There are a sol group, a benzocarbazole group, a naphthobenzofuran group, a benzonaphthothiophene group, an indenocarbazole group, a triazinyl group, and the like, but are not limited thereto.

In the present specification, the description of the above-mentioned heterocyclic group may be applied except that the heteroaryl group is aromatic.

In the present specification, the description of the aryl group may be applied except that the arylene group is divalent.

In the present specification, the description of the heterocyclic group may be applied, except that the divalent heterocycle is divalent.

In the present specification, in a substituted or unsubstituted ring formed by bonding with an adjacent group, "ring" is a hydrocarbon ring; or a heterocyclic ring.

The hydrocarbon ring may be an aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and may be selected from examples of the cycloalkyl group or the aryl group.

In the present specification, the meaning of forming a ring by bonding with adjacent groups means a substituted or unsubstituted aliphatic hydrocarbon ring by bonding with adjacent groups; a substituted or unsubstituted aromatic hydrocarbon ring; substituted or unsubstituted aliphatic heterocycle; substituted or unsubstituted aromatic heterocycle; Or it means to form a condensed ring thereof. The hydrocarbon ring means a ring consisting only of carbon and hydrogen atoms. The heterocycle means a ring including at least one selected from elements such as N, O, P, S, Si and Se. In the present specification, the aliphatic hydrocarbon ring, the aromatic hydrocarbon ring, the aliphatic heterocycle and the aromatic heterocycle may be monocyclic or polycyclic.

In the present specification, the aliphatic hydrocarbon ring refers to a ring made of only carbon and hydrogen atoms as a non-aromatic ring. Examples of the aliphatic hydrocarbon ring include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, and the like, However, the present invention is not limited thereto.

In the present specification, the aromatic hydrocarbon ring means an aromatic ring consisting only of carbon and hydrogen atoms. Examples of the aromatic hydrocarbon ring include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, chrysene, pentacene, fluorene, indene, acenaphthylene, benzofluorene, spirofluorene, and the like, but is not limited thereto. In the present specification, the aromatic hydrocarbon ring may be interpreted as having the same meaning as the aryl group.

In the present specification, the aliphatic heterocycle refers to an aliphatic ring including one or more heteroatoms. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, azocaine , thiocaine, and the like, but are not limited thereto.

In the present specification, the aromatic heterocycle refers to an aromatic ring including one or more heteroatoms. Examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, paraazole, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole, thiazole. Diazole, dithiazole, tetrazole, pyran, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinone, quinazoline, quinoxaline, naphthyridine, acridine , phenanthridine, diazanaphthalene, driazaindene, indole, indolizine, benzothiazole, benzoxazole, benzoimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzo carbazole, dibenzocarbazole, phenazine, imidazopyridine, phenoxazine, indolocarbazole, indenocarbazole, and the like, but is not limited thereto.

Hereinafter, preferred embodiments of the present invention will be described in detail. However, the embodiment of the present invention may be modified in various forms, and the scope of the present invention is not limited to the embodiments described below.

When the compound represented by Formula 1 of the present invention is applied to an organic light emitting device, an organic light emitting device having high efficiency, low voltage and/or long life can be obtained.

Hereinafter, Formula 1 will be described in detail.

[Formula 1]

In Formula 1,

Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

L1 to L6 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,

At least one of L5 and L6 is an arylene group consisting of a substituted or unsubstituted monocyclic ring; Or a substituted or unsubstituted tricyclic or more arylene group,

a and b are each an integer of 0 to 3, and when a and b are each 2 or more, L5 and L6 are each the same as or different from each other,

a+b is greater than or equal to 1.

In an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

In an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently an aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms; or a heterocyclic group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms; or a heterocyclic group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted fluorenyl group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.

In an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted fluorenyl group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.

In an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with an aryl group; a biphenyl group unsubstituted or substituted with an aryl group; a naphthyl group unsubstituted or substituted with an aryl group; a fluorenyl group unsubstituted or substituted with an alkyl group or an aryl group; dibenzofuran group; or a dibenzothiophene group.

In an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a naphthyl group; biphenyl group; naphthyl group; dimethyl fluorenyl group; or a dibenzofuran group.

In an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and are each independently represented by any one of the following structural formulas.

In the structural formula, the dotted line means the bonding position,

R6 is a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

In an exemplary embodiment of the present specification, R6 is a substituted or unsubstituted methyl group; or a substituted or unsubstituted phenyl group.

In an exemplary embodiment of the present specification, R6 is a methyl group.

In an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and are each independently represented by any one of the following structural formulas.

In the above structural formula, the dotted line means a bonding position.

In an exemplary embodiment of the present specification, L1 to L6 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted arylene group.

In an exemplary embodiment of the present specification, L1 to L6 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

In an exemplary embodiment of the present specification, L1 to L6 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In an exemplary embodiment of the present specification, L1 to L6 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; a substituted or unsubstituted terphenylene group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted phenanthrenylene group; or a substituted or unsubstituted divalent fluorene group.

In one embodiment of the present specification, L1 to L4 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted arylene group.

In one embodiment of the present specification, L1 to L4 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

In one embodiment of the present specification, L1 to L4 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In one embodiment of the present specification, L1 to L4 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; a substituted or unsubstituted terphenylene group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted phenanthrenylene group; or a substituted or unsubstituted divalent fluorene group.

In one embodiment of the present specification, L1 to L4 are the same as or different from each other, and each independently a direct bond; phenylene group; or a biphenylene group.

In one embodiment of the present specification, L1 to L4 are the same as or different from each other, and each independently a direct bond; or a phenylene group.

In an exemplary embodiment of the present specification, L1 to L4 are a direct bond, the same as or different from each other, and are each independently represented by any one of the following structural formulas.

In the above structural formula, the dotted line means a bonding position.

In an exemplary embodiment of the present specification, L5 and L6 are the same as or different from each other, and each independently an arylene group consisting of a substituted or unsubstituted monocyclic ring; or a substituted or unsubstituted tricyclic or more arylene group.

In an exemplary embodiment of the present specification, L5 and L6 are the same as or different from each other, and each independently an arylene group consisting of a substituted or unsubstituted monocyclic ring having 6 to 60 carbon atoms; or a substituted or unsubstituted C13 to C60 tricyclic or more arylene group.

In an exemplary embodiment of the present specification, L5 and L6 are the same as or different from each other, and each independently an arylene group consisting of a substituted or unsubstituted monocyclic ring having 6 to 30 carbon atoms; or a substituted or unsubstituted C13 to C30 tricyclic or more arylene group.

In an exemplary embodiment of the present specification, L5 and L6 are the same as or different from each other, and each independently represents an arylene group consisting of a substituted or unsubstituted monocyclic ring having 6 to 30 carbon atoms.

In an exemplary embodiment of the present specification, L5 and L6 are the same as or different from each other, and each independently a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; a substituted or unsubstituted phenanthrenylene group; or a substituted or unsubstituted divalent fluorene group.

In an exemplary embodiment of the present specification, L5 and L6 are the same as or different from each other, and each independently a substituted or unsubstituted phenylene group; Or a substituted or unsubstituted biphenylene group.

In an exemplary embodiment of the present specification, L5 and L6 are the same as or different from each other, and each independently a phenylene group; or a biphenylene group.

In an exemplary embodiment of the present specification, L5 and L6 are the same as or different from each other, and are each independently represented by any one of the following structural formulas.

In the above structural formula, the dotted line means a bonding position.

In an exemplary embodiment of the present specification, at least one of L5 and L6 is an arylene group consisting of a substituted or unsubstituted monocyclic ring; or a substituted or unsubstituted tricyclic or more arylene group.

In an exemplary embodiment of the present specification, at least one of L5 and L6 is a monocyclic arylene group; or an arylene group of three or more rings.

In an exemplary embodiment of the present specification, at least one of L5 and L6 is a substituted or unsubstituted phenylene group; Or a substituted or unsubstituted biphenylene group.

In an exemplary embodiment of the present specification, at least one of L5 and L6 is a phenylene group; or a biphenylene group.

In an exemplary embodiment of the present specification, L5 and L6 are the same as or different from each other, and each independently an arylene group consisting of a substituted or unsubstituted monocyclic ring; or a substituted or unsubstituted tricyclic or more arylene group.

In an exemplary embodiment of the present specification, L5 is a direct bond, L6 is an arylene group consisting of a substituted or unsubstituted monocyclic ring; or a substituted or unsubstituted tricyclic or more arylene group.

In an exemplary embodiment of the present specification, L5 is an arylene group consisting of a substituted or unsubstituted monocyclic ring; or a substituted or unsubstituted tricyclic or more arylene group, and L6 is a direct bond.

In an exemplary embodiment of the present specification, L5 and L6 are the same as or different from each other, and each independently an arylene group consisting of a substituted or unsubstituted monocyclic ring; or a substituted or unsubstituted three or more ring arylene group, wherein at least one of L5 and L6 is a substituted or unsubstituted phenylene group; Or a substituted or unsubstituted biphenylene group.

In an exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently an aryl group having 6 to 30 carbon atoms, which is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms; or a heterocyclic group having 2 to 30 carbon atoms, L1 to L4 are the same as or different from each other, and each independently a direct bond; or an arylene group having 6 to 30 carbon atoms, L5 and L6 are the same as or different from each other, and each independently an arylene group having 6 to 30 carbon atoms consisting of a monocyclic ring.

In one embodiment of the present specification, a and b are each an integer of 0 to 2.

In one embodiment of the present specification, a and b are 0 or 1, respectively.

In one embodiment of the present specification, a and b are 1 or 2, respectively.

In one embodiment of the present specification, a and b are 1.

In one embodiment of the present specification, a is 0, and b is 1.

In one embodiment of the present specification, a is 1, and b is 0.

In an exemplary embodiment of the present specification, a is 1, and b is 1.

In one embodiment of the present specification, a + b is 1 or more.

In one embodiment of the present specification, a + b is 2 or more.

In one embodiment of the present specification, a + b is 1.

In one embodiment of the present specification, a + b is 2.

In the exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-3.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Formulas 1-1 to 1-3,

Ar1 to Ar4 and L1 to L4 have the same definitions as in Formula 1 above,

L51 and L61 are the same as or different from each other, and each independently an arylene group consisting of a substituted or unsubstituted monocyclic ring; Or a substituted or unsubstituted tricyclic or more arylene group,

m and n are each an integer of 1 to 3, and when m and n are each 2 or more, L51 and L61 are respectively the same as or different from each other.

In one embodiment of the present specification, m and n are 1 or 2, respectively.

In one embodiment of the present specification, m and n are 1.

In the exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulas 2-1 to 2-3.

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

In Formulas 2-1 to 2-3,

Ar1 to Ar4 and L1 to L4 have the same definitions as in Formula 1 above,

L51 is the same as or different from each other, and each independently an arylene group consisting of a substituted or unsubstituted monocyclic ring; Or a substituted or unsubstituted tricyclic or more arylene group,

m is an integer of 1 to 3, and when m is 2 or more, L51 of 2 or more are the same as or different from each other.

In an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of the following compounds.

The compound represented by Formula 1 according to an exemplary embodiment of the present specification may have a core structure as shown in Scheme 1 below. Substituents may be combined by methods known in the art, and the type, position or number of substituents may be changed according to techniques known in the art.

<Scheme 1>

In Scheme 1, the definition of the substituent is the same as the definition in Formula 1 above, Z1 and Z2 are the same as or different from each other, and each independently represents a halogen group (-Cl, -Br, etc.).

In Scheme 1, the process of synthesizing a compound in which a specific substituent is bonded to a specific position is exemplified. Compounds corresponding to the range can be synthesized.

In the present specification, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure of the compound represented by Formula 1 above. In addition, in the present specification, the HOMO and LUMO energy levels of the compound can be controlled by introducing various substituents into the core structure of the structure as described above.

In addition, the present specification provides an organic light emitting device including the above-described compound.

In the present specification, when a member is said to be located “on” another member, this includes not only a case in which a member is in contact with another member but also a case in which another member is present between the two members.

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.

The organic light emitting device according to the present specification includes an anode; cathode; and at least one organic material layer provided between the anode and the cathode, wherein at least one of the organic material layers comprises a compound represented by Formula 1 above.

The organic light emitting device of the present specification may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except for forming an organic material layer using the compound of Formula 1 above.

The compound may be formed into 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, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

The organic material layer of the organic light emitting 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, the organic light emitting device of the present invention comprises at least one of a hole transport layer, a hole injection layer, an electron blocking layer, a hole transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron transport and injection layer as an organic material layer. It may have a structure containing However, the structure of the organic light emitting device of the present specification is not limited thereto and may include a smaller number or a larger number of organic material layers.

In the organic light emitting device of the present specification, the organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer is a compound represented by Formula 1 described above. may include

In the organic light emitting device of the present specification, the organic material layer may include a hole transport layer or a hole injection layer, and the hole transport layer or the hole injection layer may include the compound represented by Chemical Formula 1 described above.

In an exemplary embodiment of the present specification, the organic material layer includes an electron blocking layer, and the electron blocking layer includes a compound represented by Formula 1 above.

In one embodiment of the present specification, the organic material layer includes an electron injection layer, an electron transport layer, an electron transport and injection layer or a hole blocking layer, and the electron injection layer, the electron transport layer, the electron transport and injection layer or the hole blocking layer is It may include a compound represented by Formula 1 described above.

In the organic light emitting device of the present specification, the organic material layer includes an electron transport layer, an electron injection layer, or an electron transport and injection layer, and the electron transport layer, the electron injection layer, or the electron transport and injection layer is represented by the above formula (1) compounds may be included.

In an exemplary embodiment of the present specification, the organic material layer may include an electron control layer, and the electron control layer may include the compound represented by Formula 1 described above.

In an exemplary embodiment of the present specification, the organic material layer includes a hole blocking layer, and the hole blocking layer includes a compound represented by Formula 1 above.

In the organic light emitting device of the present specification, the organic material layer is an electron transport and injection layer, and the electron transport and injection layer includes the compound represented by Chemical Formula 1 described above.

In the exemplary embodiment of the present specification, the thickness of the organic material layer including the compound of Formula 1 is 5 Å to 2000 Å, preferably 100 Å to 1500 Å.

In an exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound represented by Formula 1 above.

In an exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes the compound represented by Formula 1 as a host.

In the exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes the compound represented by Formula 1 as a dopant.

In another exemplary embodiment, the organic material layer may further include other organic compounds, metals, or metal compounds in addition to the compound represented by Formula 1 above.

In the organic light emitting device according to the exemplary embodiment of the present specification, the light emitting layer further includes a fluorescent dopant or a phosphorescent dopant. In this case, the dopant in the emission layer is included in an amount of 1 to 50 parts by weight based on 100 parts by weight of the host.

As another example, the organic material layer may include an emission layer, the emission layer may include the compound represented by Formula 1 as a host, and may further include an additional host.

In the exemplary embodiment of the present specification, the dopant includes an arylamine-based compound, a heterocyclic compound including boron and nitrogen, or an Ir complex.

The organic light emitting device of the present specification may further include at least one organic material layer of a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole injection and transport layer. have.

In an exemplary embodiment of the present specification, the organic light emitting device includes an anode; cathode; and two or more organic material layers provided between the anode and the cathode, wherein at least one of the two or more organic material layers includes the compound represented by Formula 1 above.

In an exemplary embodiment of the present specification, two or more organic material layers may be selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, a hole transport and injection layer, and an electron blocking layer.

In an exemplary embodiment of the present specification, two or more organic material layers may be selected from the group consisting of a light emitting layer, an electron transport layer, an electron injection layer, an electron transport and injection layer, an electron control layer, and a hole blocking layer.

In the exemplary embodiment of the present specification, the organic material layer includes two or more electron transport layers, and at least one of the two or more electron transport layers includes the compound represented by Formula 1 above. Specifically, in an exemplary embodiment of the present specification, the compound represented by Formula 1 may be included in one of the two or more electron transport layers, and may be included in each of the two or more electron transport layers.

In addition, in the exemplary embodiment of the present specification, when the compound is included in each of the two or more electron transport layers, materials other than the compound represented by Formula 1 may be the same or different from each other.

When the organic material layer including the compound represented by Formula 1 is an electron transport layer, an electron injection layer, or an electron transport and injection layer, the electron transport layer, the electron injection layer, or the electron transport and injection layer is an n-type dopant or an organometallic compound may further include. As the n-type dopant or organometallic compound, those known in the art may be used, for example, a metal or a metal complex may be used.

For example, the n-type dopant or the organometallic compound may be LiQ, but is not limited thereto. The electron transport layer, the electron injection layer, or the electron transport and injection layer including the compound represented by Formula 1 may further include lithium quinolate (LiQ).

According to an example, the compound represented by Formula 1 and the n-type dopant or the organometallic compound may be included in a weight ratio of 2:8 to 8:2, for example, 4:6 to 6:4. According to an example, the compound represented by Formula 1 and the n-type dopant or organometallic compound may be included in a weight ratio of 1:1.

In an exemplary embodiment of the present specification, the organic material layer includes two or more hole transport layers, and at least one of the two or more hole transport layers includes the compound represented by Formula 1 above. Specifically, in an exemplary embodiment of the present specification, the compound represented by Formula 1 may be included in one of the two or more hole transporting layers, and may be included in each of the two or more hole transporting layers.

In addition, in an exemplary embodiment of the present specification, when the compound represented by Formula 1 is included in each of the two or more hole transport layers, materials other than the compound represented by Formula 1 may be the same or different from each other. have.

In an exemplary embodiment of the present specification, the organic material layer includes a hole injection layer or a hole transport layer including a compound including an arylamine group, a carbazolyl group or a benzocarbazolyl group in addition to the organic material layer including the compound represented by Formula 1 may include

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

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

In the organic light emitting device of the present invention, the organic material layer may include an electron blocking layer, and a material known in the art may be used for the electron blocking layer.

The organic light emitting diode may have, for example, a stacked structure as follows, but is not limited thereto.

(1) Anode / hole transport layer / light emitting layer / cathode

(2) anode / hole injection layer / hole transport layer / light emitting layer / cathode

(3) anode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / cathode

(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 blocking layer / light emitting layer / electron transport layer / cathode

(11) anode / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / electron injection layer / cathode

(12) anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / cathode

(13) anode / hole injection layer / hole transport layer / electron blocking 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 / cathode

(15) anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

(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 / cathode

(18) anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / hole blocking layer / electron transport and injection layer / cathode

The structure of the organic light emitting device of the present specification may have a structure as shown in FIGS. 1 to 3 , but is not limited thereto.

1 shows an example of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 6, and a cathode 10 are sequentially stacked. In such a structure, the compound may be included in the light emitting layer 6 .

2 is a substrate (1), anode (2), hole injection layer (3), hole transport layer (4), electron blocking layer (5), light emitting layer (6), hole blocking layer (7), electron transport layer (8) , an example of an organic light emitting device in which the electron injection layer 9 and the cathode 10 are sequentially stacked. In this structure, the compound is a hole injection layer (3), a hole transport layer (4), an electron blocking layer (5), a light emitting layer (6), a hole blocking layer (7), an electron transport layer (8) or an electron injection layer (9) may be included.

3 shows a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, a hole blocking layer 7, an electron transport and injection layer An example of an organic light emitting device in which (11) and the cathode (10) are sequentially stacked is shown. In this structure, the compound is a hole injection layer (3), a hole transport layer (4), an electron blocking layer (5), a light emitting layer (6), a hole blocking layer (7) or an electron transport and injection layer (11) may be included.

In one embodiment of the present specification, the electron blocking layer and the light emitting layer may be provided adjacent to each other. For example, the electron blocking layer and the light emitting layer may be provided in physical contact with each other.

In one embodiment of the present specification, the hole transport layer and the electron blocking layer may be provided adjacent to each other. For example, the hole transport layer and the electron blocking layer may be provided in physical contact.

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

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 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 conductive metal oxide or an alloy thereof on a substrate. is deposited to form an anode, and an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, an electron transport layer and an electron injection layer is formed thereon, and then a material that can be used as a cathode is deposited thereon. can be In addition to this method, an organic light emitting 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 may further include one or more of a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole injection and transport layer.

The organic material layer may have a multilayer structure including a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, a light emitting layer and an electron transport layer, an electron injection layer, an electron transport and injection layer, etc., but is not limited thereto, and may have a single layer structure can 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 the anode material is preferably a material having a large work function 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 multi-layered material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

The hole injection layer is a layer that smoothly injects holes from the anode into the light emitting layer. As the hole injection material, holes can be well injected from the anode at a low voltage. 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, polyaniline and polythiophene-based conductive polymers, and the like, but are not limited thereto. The hole injection layer may have a thickness of 1 nm to 150 nm. When the thickness of the hole injection layer is 1 nm or more, there is an advantage in that the hole injection characteristics can be prevented from being deteriorated, and when it is 150 nm or less, the thickness of the hole injection layer is too thick, so that the driving voltage is increased to improve hole movement. It has the advantage of preventing it from rising.

In an exemplary embodiment of the present specification, the hole injection layer may include an arylamine compound including a carbazole group and a p-type dopant. According to one embodiment, the amine compound is represented as Het101-L101-N(Ar101)(Ar102), Het101 is a substituted or unsubstituted carbazole group, L101 is a substituted or unsubstituted arylene group, Ar101 and Ar102 are the same as or different from each other, and may each independently be a substituted or unsubstituted aryl group. The amine compound and the p-type dopant may be included in an appropriate molar ratio, and according to an example, the amine compound and the p-type dopant may be included in a molar ratio of 99.9:0.1 to 90:10.

The hole transport layer may serve to facilitate hole transport. As the hole transport material, a material capable of transporting holes from the anode or hole injection layer 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.

In an exemplary embodiment of the present specification, the hole transport layer may include a compound represented by Formula 1 of the present invention.

An additional hole buffer layer may be provided between the hole injection layer and the hole transport layer, and may include hole injection or transport materials known in the art.

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

In an exemplary embodiment of the present specification, the electron blocking layer may include an arylamine compound including a carbazole group. According to one embodiment, the amine compound is represented as Het101-L101-N(Ar101)(Ar102), Het101 is a substituted or unsubstituted carbazole group, L101 is a substituted or unsubstituted arylene group, Ar101 and Ar102 are the same as or different from each other, and may each independently be a substituted or unsubstituted aryl group.

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. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene, rubrene, and the like, but is not limited thereto.

Examples of the host material for the light emitting layer include a condensed aromatic ring derivative or a heterocyclic compound containing compound. 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, a phosphor such as Ir(ppy) ₃ (fac tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq3 (tris(8-hydroxyquinolino)aluminum) may be used as the emission dopant. However, the present invention 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 or a PPV-based polymer may be used, but is not limited thereto.

In an exemplary embodiment of the present specification, the light emitting layer may include an anthracene compound substituted with an aryl group or a heterocyclic group as a host, and a pyrene compound substituted with an amine group as a dopant. According to an example, the anthracene compound may have a structure in which carbons 9 and 10 are substituted with an aryl group or a heterocyclic group. The host and the dopant may be included in an appropriate weight ratio, and according to an example, the host and the dopant may be included in a weight ratio of 100:1 to 100:10.

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

In an exemplary embodiment of the present specification, the hole blocking layer may include a compound including an N-containing heterocyclic group and a fluorene ring.

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 the above-mentioned compound or Al complex of 8-hydroxyquinoline; complexes comprising Alq ₃ ; organic radical compounds; hydroxyflavone-metal complexes, and the like, but are not limited thereto. The thickness of the electron transport layer may be 1 nm to 50 nm. If the thickness of the electron transport layer is 1 nm or more, there is an advantage that the electron transport characteristics can be prevented from being deteriorated, and if it is 50 nm or less, the thickness of the electron transport layer is too thick, so that the driving voltage is increased to improve the movement of electrons There are advantages to avoiding it.

In an exemplary embodiment of the present specification, the electron transport layer may include a compound including two N-containing heterocyclic groups, and may further include an n-type dopant or an organometallic compound. According to an example, the n-type dopant or the organometallic compound may be LiQ, and the compound including the two N-containing heterocyclic groups and the n-type dopant (or organometallic compound) are 2:8 to 8:2, For example, it may be included in a weight ratio of 4:6 to 6:4.

The electron injection layer may serve to facilitate electron injection. 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 hole blocking layer is a layer that blocks the holes from reaching the cathode, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complex, and the like, but is not limited thereto.

The organic light emitting device according to the present invention may be a top emission type, a back emission type, or a double side emission type depending on the material used.

The organic light emitting diode according to the present specification may be included in various electronic devices. For example, the electronic device may be a display panel, a touch panel, a solar module, a lighting device, and the like, but is not limited thereto.

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

<Production Example 1>

After completely dissolving compound 1,2-bis(4-chlorophenyl)naphthalene (5.88 g, 16.85 mmol), and compound a-1 (6.26 g, 37.07 mmol) in 310 mL of xylene in a 500 mL round bottom flask in a nitrogen atmosphere, NaOtBu (4.05 g, 42.12 mmol) was added, and Bis(tri- tert -butylphosphine) palladium(0) (0.43 g, 0.84 mmol) was added thereto, followed by heating and stirring for 4 hours. After lowering the temperature to room temperature and removing the base by filtration, xylene was concentrated under reduced pressure and recrystallized from 230 mL of ethyl acetate to prepare compound 1 (6.44 g, yield: 62%).

MS[M+H] ⁺ = 615

<Production Example 2>

After completely dissolving compound 1,2-bis(4-chlorophenyl)naphthalene (6.11 g, 17.51 mmol), and compound a-2 (8.43 g, 38.52 mmol) in 270 mL of xylene in a 500 mL round bottom flask in a nitrogen atmosphere, NaOtBu (4.21 g, 43.77 mmol) was added, and Bis(tri- tert -butylphosphine) palladium(0)(0.45 g, 0.88 mmol) was added thereto, followed by heating and stirring for 4 hours. After lowering the temperature to room temperature and removing the base by filtration, xylene was concentrated under reduced pressure and recrystallized from 250 mL of ethyl acetate to prepare compound 2 (7.36 g, yield: 59%).

MS[M+H] ⁺ = 715

<Production Example 3>

After completely dissolving compound 1,2-bis(3-chlorophenyl)naphthalene (6.25 g, 17.91 mmol), and compound a-3 (9.65 g, 39.40 mmol) in 280 mL of xylene in a 500 mL round bottom flask in a nitrogen atmosphere, NaOtBu (4.30 g, 44.77 mmol) was added, and Bis(tri- tert -butylphosphine) palladium(0) (0.46 g, 0.90 mmol) was added thereto, followed by heating and stirring for 4 hours. After lowering the temperature to room temperature and removing the base by filtration, xylene was concentrated under reduced pressure and recrystallized from 260 mL of ethyl acetate to prepare compound 3 (8.19 g, yield: 60%).

MS[M+H] ⁺ = 767

<Production Example 4>

Compound 4-(2-(4-chlorophenyl)naphthalen-1-yl)-N,N-diphenylaniline (7.62 g, 15.81 mmol), and compound a-4 (5.13 g, 17.39) in a 500 mL round bottom flask under nitrogen atmosphere mmol) was completely dissolved in 280 mL of xylene, NaOtBu (2.28 g, 23.71 mmol) was added, Bis(tri- tert -butylphosphine) palladium(0) (0.40 g, 0.79 mmol) was added, and then heated and stirred for 5 hours. did. After lowering the temperature to room temperature and removing the base by filtration, xylene was concentrated under reduced pressure, and recrystallized from 310 mL of ethyl acetate to prepare compound 4 (7.34 g, yield: 63%).

MS[M+H] ⁺ = 741

<Preparation Example 5>

Compound 4-(1-(4-chlorophenyl)naphthalen-2-yl)-N,N-diphenylaniline (7.23 g, 15.00 mmol), and compound a-5 (4.87 g, 16.50) in a 500 mL round bottom flask under nitrogen atmosphere mmol) was completely dissolved in 250 mL of xylene, NaOtBu (4.87 g, 16.50 mmol) was added, Bis(tri- tert -butylphosphine) palladium(0) (0.38 g, 0.75 mmol) was added, and then heated and stirred for 4 hours. did. After lowering the temperature to room temperature and removing the base by filtration, xylene was concentrated under reduced pressure and recrystallized from 250 mL of ethyl acetate to prepare compound 5 (7.71 g, yield: 69%).

MS[M+H] ⁺ = 741

<Preparation Example 6>

Compound 4-(2-chloronaphthalen-1-yl)-N,N-diphenylaniline (6.88 g, 16.95 mmol), and compound a-6 (5.98 g, 18.64 mmol) in xylene in a 500 mL round bottom flask under nitrogen atmosphere After completely dissolving in 260 mL, NaOtBu (2.44 g, 25.42 mmol) was added, Bis(tri- tert -butylphosphine) palladium(0)(0.43 g, 0.85 mmol) was added, and then heated and stirred for 7 hours. After lowering the temperature to room temperature and removing the base by filtration, xylene was concentrated under reduced pressure and recrystallized from 310 mL of ethyl acetate to prepare compound 6 (6.87 g, yield: 59%).

MS[M+H] ⁺ = 691

<Production Example 7>

Compound 4-(1-bromonaphthalen-2-yl)-N,N-diphenylaniline (6.53 g, 14.51 mmol), and compound a-7 (5.76 g, 15.96 mmol) in xylene in a 500 mL round bottom flask under nitrogen atmosphere. After it was completely dissolved in 290 mL, NaOtBu (2.09 g, 21.77 mmol) was added, and Bis(tri- tert -butylphosphine) palladium(0) (0.37 g, 0.73 mmol) was added thereto, followed by heating and stirring for 5 hours. After lowering the temperature to room temperature and removing the base by filtration, xylene was concentrated under reduced pressure and recrystallized from 280 mL of ethyl acetate to prepare compound 7 (5.98 g, yield: 56%).

MS[M+H] ⁺ = 731

<Preparation Example 8>

Compound 4'-(2-chloronaphthalen-1-yl)-N,N-diphenyl-[1,1'-biphenyl]-4-amine (6.88 g, 14.27 mmol), and Compound a-8 (4.47 g, 15.70 mmol) was completely dissolved in 290 mL of xylene, NaOtBu (2.06 g, 21.41 mmol) was added, and Bis(tri- tert -butylphosphine) palladium(0)(0.36 g, 0.71 mmol) was added. ) and then heated and stirred for 5 hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized from 290 mL of ethyl acetate to prepare compound 8 (7.25 g, yield: 69%).

MS[M+H] ⁺ = 731

<Production Example 9>

Compound 4'-(1-chloronaphthalen-2-yl)-N,N-diphenyl-[1,1'-biphenyl]-4-amine (6.33 g, 13.13 mmol), and After completely dissolving compound a-9 (3.74 g, 14.45 mmol) in 280 mL of xylene, NaOtBu (1.89 g, 19.70 mmol) was added, and Bis(tri- tert -butylphosphine) palladium(0)(0.34 g, 0.66 mmol) was added. ) and then heated and stirred for 5 hours. After lowering the temperature to room temperature and filtering to remove the base, xylene was concentrated under reduced pressure and recrystallized from ethyl acetate 240 mL to prepare compound 8 (6.88 g, yield: 74%).

MS[M+H] ⁺ = 705

<Example 1-1>

A glass substrate coated with indium tin oxide (ITO) to a thickness of 1,000 Å was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a product manufactured by Fischer Co. was used as the detergent, and distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water. After washing ITO for 30 minutes, ultrasonic cleaning was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, and after drying, it was 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-depositing a compound of the following compound HI1 and a compound of the following compound HI2 to a thickness of 100 Å in a ratio of 98:2 (molar ratio) on the prepared anode, ITO transparent electrode. Compound 1 (1150 Å) prepared in Preparation Example 1 was vacuum deposited on the hole injection layer to form a hole transport layer. Then, a compound of EB1 was vacuum-deposited to a thickness of 50 Å on the hole transport layer to form an electron blocking layer. Then, the compound represented by the following formula BH and the compound represented by the following formula BD to a thickness of 200 Å on the electron blocking layer were vacuum-deposited in a weight ratio of 25:1 to form a light emitting layer. A hole blocking layer was formed by vacuum-depositing a compound represented by Formula HB1 to a film thickness of 50 Å on the light emitting layer. Then, on the hole blocking layer, the compound represented by the formula ET1 and the compound represented by the formula LiQ were vacuum-deposited in a weight ratio of 1:1 to form an electron transport and injection layer to a thickness of 310 Å. A cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 12 Å and aluminum to a thickness of 1,000 Å on the electron transport and injection layer.

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 of the negative electrode was maintained at 0.3Å/sec, and the deposition rate of aluminum was maintained at 2Å/sec, and the vacuum degree during deposition was 2×10 ^-7 ~ By maintaining 5×10 ^-6 torr, an organic light emitting device was manufactured.

<Examples 1-2 to Examples 1-9>

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

<Comparative Examples 1-1 to 1-3>

An organic light emitting diode was manufactured in the same manner as in Example 1-1, except that the compound shown in Table 1 was used instead of Compound 1. The compounds of HT-1, HT-2 and HT-3 used in Table 1 below are as follows.

When a current was applied to the organic light emitting diodes prepared in Examples and Comparative Examples, voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in Table 1 below. T95 denotes a time required for the luminance to decrease from the initial luminance (1600 nit) to 95%.

compound
(hole transport layer) Voltage
(V@10mA
/cm ² ) efficiency
(cd/A@10mA
/cm ² ) color coordinates
(x,y) T95
(hr) Example 1-1 compound 1 4.31 6.50 (0.146, 0.046) 260 Example 1-2 compound 2 4.33 6.53 (0.145, 0.046) 265 Examples 1-3 compound 3 4.47 6.47 (0.146, 0.047) 255 Examples 1-4 compound 4 4.49 6.39 (0.147, 0.046) 270 Examples 1-5 compound 5 4.42 6.38 (0.146, 0.045) 275 Examples 1-6 compound 6 4.45 6.44 (0.146, 0.046) 275 Examples 1-7 compound 7 4.44 6.45 (0.146, 0.046) 265 Examples 1-8 compound 8 4.50 6.45 (0.147, 0.046) 245 Examples 1-9 compound 9 4.53 6.46 (0.147, 0.047) 255 Comparative Example 1-1 HT-1 5.12 5.22 (0.146, 0.047) 85 Comparative Example 1-2 HT-2 4.98 5.35 (0.145, 0.046) 115 Comparative Example 1-3 HT-3 4.87 5.83 (0.144, 0.045) 160

As shown in Table 1, the organic light emitting device using the compound of the present invention exhibited excellent characteristics in terms of efficiency, driving voltage, and stability of the organic light emitting device. Specifically, in Examples 1-1 to 1-9, , The organic light emitting device using the compound of the present invention includes two naphthylene linkers between two amine groups, consists of a direct bond without a linker, or HT-1, HT- 2, the organic light emitting device of Comparative Examples 1-1, 1-2, and 1-3 manufactured using the material of HT-3 showed characteristics of lower voltage, high efficiency, and longer lifespan.

Although preferred embodiments of the present invention have been described above, the present invention is not limited thereto, and it is possible to carry out various modifications within the scope of the claims and the detailed description of the invention, and this also falls within the scope of the invention. .

1: substrate
2: Anode
3: hole injection layer
4: hole transport layer
5: Electron blocking layer
6: light emitting layer
7: hole blocking layer
8: electron transport layer
9: electron injection layer
10: cathode
11: Electron transport and injection layer

Claims (10)

A compound represented by the following formula (1):
[Formula 1]

In Formula 1,
Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
L1 to L6 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,
At least one of L5 and L6 is an arylene group consisting of a substituted or unsubstituted monocyclic ring; Or a substituted or unsubstituted tricyclic or more arylene group,
a and b are each an integer of 0 to 3, and when a and b are each 2 or more, L5 and L6 are each the same as or different from each other,
a+b is greater than or equal to 1. The method according to claim 1,
Formula 1 is a compound represented by any one of the following Formulas 1-1 to 1-3:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Formulas 1-1 to 1-3,
Ar1 to Ar4 and L1 to L4 have the same definitions as in Formula 1 above,
L51 and L61 are the same as or different from each other, and each independently an arylene group consisting of a substituted or unsubstituted monocyclic ring; Or a substituted or unsubstituted tricyclic or more arylene group,
m and n are each an integer of 1 to 3, and when m and n are each 2 or more, L51 and L61 are respectively the same as or different from each other. The method according to claim 1, wherein L5 and L6 are the same as or different from each other, and each independently an arylene group consisting of a substituted or unsubstituted monocyclic ring; Or a substituted or unsubstituted tricyclic or more arylene group,
At least one of L5 and L6 is a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylene group. The method according to claim 1, wherein Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted fluorenyl group; A substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group. The method according to claim 1, wherein Ar1 to Ar4 are the same as or different from each other, and each independently an aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms; Or a heterocyclic group having 2 to 30 carbon atoms,
L1 to L4 are the same as or different from each other, and each independently a direct bond; or an arylene group having 6 to 30 carbon atoms,
L5 and L6 are the same as or different from each other, and each independently represents a monocyclic arylene group having 6 to 30 carbon atoms. The compound according to claim 1, wherein Formula 1 is represented by any one of the following compounds:

. anode; cathode; and at least one organic material layer provided between the anode and the cathode, wherein at least one of the organic material layers comprises the compound according to any one of claims 1 to 6. 8. The method of claim 7,
The organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer is an organic light emitting device that includes the compound. 8. The method of claim 7,
The organic material layer includes an electron blocking layer, and the electron blocking layer includes the compound. 8. The method of claim 7,
The organic material layer further comprises at least one of a hole transport layer, a hole injection layer, an electron blocking layer, a hole injection and transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron transport and injection layer. .

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