KR20230083039A - Compound and organic light emitting device comprising same - Google Patents

Abstract

The present specification provides a compound represented by chemical formula 1 and an organic light emitting device containing the same. The compound described in the present specification can be used as a material for an organic material layer of the organic light emitting device. The compound according to at least one embodiment of the present specification can improve efficiency, lower driving voltage, and/or improve lifespan characteristics in the organic light emitting device.

Description

Compound and an organic light emitting device including the same {COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING 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 electrical energy is converted into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is often composed of a multi-layer structure composed of different materials 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, and an electron injection layer. In the structure of this 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 when the injected holes and electrons meet, excitons are formed. When it falls back to the ground state, it glows.

Development of new materials for the organic light emitting device as described above has been continuously demanded.

Korean Patent Publication No. 10-2011-0084798

In the present specification, a compound and an organic light emitting device including the same are provided.

An exemplary embodiment of the present specification provides a compound represented by Formula 1 below.

[Formula 1]

In Formula 1,

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

Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or a nitrile group,

X1 to X3 are the same as or different from each other, and each independently N; CH; or a CD;

At least one of X1 to X3 is N,

The part where no substituent is shown on the benzene ring is substituted with H or D.

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

The compounds described in this specification can be used as a material for an organic material layer of an organic light emitting device. The compound according to at least one exemplary embodiment of the present specification may improve efficiency, low driving voltage, and/or lifetime characteristics of 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 materials. In addition, compared to conventional organic light emitting devices, there are effects of low driving voltage, high efficiency, and/or 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 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, and an electron transport layer 8 , shows an example of an organic light emitting device in which an electron injection layer 9 and a cathode 10 are sequentially stacked.
Figure 3 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 and injection layer 11 and a cathode 10 are sequentially stacked.

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

In the present specification, when a certain component is said to "include", it means that it may further include other components without excluding other components unless otherwise stated.

In this specification, when a member is said to be located “on” another member, this includes not only the case where a member is in contact with another member, but also the case where 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 of bonding to the chemical 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 hydrogen atom is substituted, that is, a position where the substituent is substituted, and when two or more are substituted , Two or more substituents may be the same as or different from each other.

In one embodiment of the present specification, the term "substituted or unsubstituted" refers to deuterium; halogen group; nitrile group (-CN); nitro group; hydroxy group; an alkyl group; cycloalkyl group; alkoxy group; phosphine oxide group; aryloxy group; Alkyl thioxy group; Arylthioxy group; an alkyl sulfoxy group; aryl sulfoxy groups; alkenyl group; silyl group; boron group; amine group; aryl group; Or substituted with one or two or more substituents selected from the group consisting of heterocyclic groups, or substituted with substituents in which two or more substituents among the above exemplified substituents are connected, or without 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.

In one embodiment of the present specification, the term "substituted or unsubstituted" refers to deuterium; halogen group; nitrile group; nitro group; hydroxy 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, or is substituted with a substituent in which two or more substituents from among the above exemplified substituents are connected, or does not have any substituents.

In one embodiment of the present specification, 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, or is substituted with a substituent in which two or more substituents from among the above exemplified substituents are connected, or does not have any substituents.

In the present specification, the term "benzene ring" means to include not only monocyclic benzene rings such as phenyl, biphenyl, and terphenyl groups, but also polycyclic benzene rings such as naphthyl, anthracenyl, and phenalthrenyl groups.

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

In the present specification, examples of the halogen group include a fluoro group (-F), a chloro group (-Cl), a bromo group (-Br), or an iodo group (-I).

In the present specification, the silyl group may be represented by a chemical 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 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, but is not limited thereto. don't

In the present specification, the boron group may be represented by the chemical formula -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. The boron group specifically includes a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, a phenyl boron group, but is not limited thereto.

In the present specification, the alkyl group may be straight or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 30. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another exemplary embodiment, the number of carbon atoms of the alkyl group is 1 to 10. 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 is 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 straight chain, branched chain or cyclic chain. The number of carbon atoms in the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. 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, etc., but is not limited thereto.

Alkyl groups, alkoxy groups, and substituents containing other alkyl moieties described herein include both straight-chain and branched 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 one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. 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, etc., but is not limited thereto.

In the present specification, the alkynyl group is a substituent including a triple bond between carbon atoms and may be straight or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkynyl group is 2 to 20. According to another embodiment, the number of carbon atoms 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 number of carbon atoms of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 6. 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 are 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 one embodiment, the carbon number of the amine group is 1 to 20. According to one embodiment, the carbon number of the amine group is 1 to 10. Specific examples of the substituted amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, 9,9-dimethylfluorenylphenylamine group, pyridylphenylamine group, diphenylamine group, phenylpyridylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, dibenzofuranylphenylamine group, 9-methylanthracenylamine group, diphenylamine group, phenylnaphthylamine group, A ditolylamine group, a phenyltolylamine group, a diphenylamine group, and the like, but are 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 one embodiment, the number of carbon atoms of the aryl group is 6 to 30. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 20. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, etc. as a monocyclic aryl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenylenyl group, chrysenyl group, fluorenyl group, triphenylenyl group, etc., but is limited thereto it is not going to be

In the present specification, the aryl group may be a monocyclic aryl group or a polycyclic aryl group (two or more ring aryl groups). An aryl group consisting of a monocyclic ring may be a phenyl group; Or it may mean a group in which two or more phenyl groups are connected. The monocyclic aryl group may include, but is not limited to, a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, and the like. The polycyclic aryl group may mean a group in which two or more monocyclic rings are condensed, such as a naphthyl group and a phenanthrenyl group. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenyl group, chrysenyl group, fluorenyl group, 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. At this time, 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-dimethylfluorenyl group), and

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

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

In the present specification, the description of the alkyl group described above may be applied to the alkyl group in the alkylthioxy group and the alkylsulfoxy group.

In the present specification, the description of the aryl group described above may be applied to the aryl group among the arylthiooxy group and the arylsulfoxy group.

In the present specification, the heterocyclic group is a ring group containing one or more of N, O, P, S, Si and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but preferably has 2 to 60 carbon atoms. According to one embodiment, the carbon number of the heterocyclic group is 2 to 30. According to one embodiment, the carbon number of the heterocyclic group is 2 to 20. 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, carba 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 heterocyclic group described above 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 heterocyclic ring is divalent.

In the present specification, in a substituted or unsubstituted ring formed by bonding with adjacent groups, "ring" refers to a hydrocarbon ring; or a heterocyclic ring.

The hydrocarbon ring may be 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; A substituted or unsubstituted aliphatic heterocycle; A substituted or unsubstituted aromatic heterocycle; or to form a condensed ring thereof. The hydrocarbon ring means a ring composed of only carbon and hydrogen atoms. The heterocycle refers to a ring containing at least one selected from elements such as N, O, P, S, Si, and Se. In the present specification, the aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic heterocycle and aromatic heterocycle may be monocyclic or polycyclic.

In the present specification, an aliphatic hydrocarbon ring is a non-aromatic ring and refers to a ring composed of only carbon and hydrogen atoms. Examples of the aliphatic hydrocarbon ring include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, etc. Not limited to this.

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

In the present specification, an aliphatic heterocycle means an aliphatic ring containing one or more of heteroatoms. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, azocaine , Thiocane, etc., but are not limited thereto.

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

Hereinafter, preferred embodiments of the present invention will be described in detail. However, the embodiments 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.

Formula 1 of the present invention is characterized in that an ortho-oriented phenylene group is connected to a monocyclic ring containing sulfonyldibenzene and N.

When the compound represented by Chemical 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 lifespan characteristics can be obtained.

Hereinafter, Formula 1 will be described in detail.

[Formula 1]

In Formula 1,

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

Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; or a nitrile group

X1 to X3 are the same as or different from each other, and each independently N; CH; or a CD;

At least one of X1 to X3 is N,

The part where no substituent is shown on the benzene ring is substituted with H or D.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenylylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted divalent fluorenyl group; A substituted or unsubstituted divalent dibenzofuran group; Or a substituted or unsubstituted divalent dibenzofuran group.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond; A phenylene group unsubstituted or substituted with heavy hydrogen; A biphenyl group unsubstituted or substituted with heavy hydrogen; A terphenyllylene group unsubstituted or substituted with heavy hydrogen; A naphthylene group unsubstituted or substituted with heavy hydrogen; A divalent fluorenyl group unsubstituted or substituted with heavy hydrogen; A divalent dibenzofuran group unsubstituted or substituted with heavy hydrogen; or a divalent dibenzofuran group unsubstituted or substituted with heavy hydrogen.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond; phenylene group; a biphenylylene group; terphenylylene group; naphthylene group; Divalent fluorenyl group; Divalent dibenzofuran group; or a divalent dibenzofuran group.

In one embodiment of the present specification, L1 and L2 are a direct bond.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond; or any one selected from the following structures.

In the above structure,

The structure is substituted or unsubstituted with deuterium,

The dotted line is connected to Formula 1 above,

R11 and R12 are the same as or different from each other, and are each independently substituted or unsubstituted hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond; or any one selected from the following structures.

In the above structure,

The dotted line is connected to Formula 1 above,

R11 and R12 are the same as or different from each other, and are each independently substituted or unsubstituted hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; or a nitrile group.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; A substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; or a nitrile group.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; or a nitrile group.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; A substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms; or a nitrile group.

In one embodiment of the present specification, Ar1 and Ar2 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 quaterphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted spirobifluorenyl group; A substituted or unsubstituted triphenylenyl group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted dibenzothiophene group; or a nitrile group.

In one embodiment of the present specification, Ar1 and Ar2 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 triphenylenyl group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted dibenzothiophene group; or a nitrile group.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with deuterium or a nitrile group; A biphenyl group unsubstituted or substituted with a deuterium or nitrile group; A terphenyl group unsubstituted or substituted with a deuterium or nitrile group; A naphthyl group unsubstituted or substituted with a deuterium or nitrile group; A phenanthrenyl group unsubstituted or substituted with a deuterium or nitrile group; a fluorenyl group unsubstituted or substituted with heavy hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a nitrile group; A triphenylenyl group unsubstituted or substituted with a deuterium or nitrile group; A dibenzofuran group unsubstituted or substituted with a deuterium or nitrile group; Dibenzothiophene group unsubstituted or substituted with deuterium or nitrile group; or a nitrile group.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group; biphenyl group; ziterphenyl group; naphthyl group; phenanthrenyl group; dimethyl fluorenyl group; Diphenyl fluorenyl group; triphenylenyl group; Dibenzofuran group; Dibenzothiophene group; or a nitrile group.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently selected from the following structures.

In the above structure,

The structure is substituted or unsubstituted with deuterium,

The dotted line is the position connected to Formula 1,

R13 and R14 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

In one embodiment of the present specification, R13 and R14 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, R13 and R14 are the same as or different from each other, and each independently a methyl group; or a phenyl group.

In one embodiment of the present specification, X1 to X3 are the same as or different from each other, and each independently N; CH; or a CD;

At least one of X1 to X3 is N.

In one embodiment of the present specification, at least one of X1 to X3 is N.

In one embodiment of the present specification, at least two of X1 to X3 are N.

In one embodiment of the present specification, X1, X2 and X3 are N.

In one embodiment of the present specification, X1 and X2 are N, X3 is CH; or CD.

In one embodiment of the present specification, X1 and X3 are N, X2 is CH; or CD.

In one embodiment of the present specification, X2 and X3 are N, and X1 is CH; or CD.

In one embodiment of the present specification, X1 is N, X2 and X3 are CH; or CD.

According to an exemplary embodiment of the present specification, X2 is N, and X1 and X3 are CH; or CD.

According to an exemplary embodiment of the present specification, X3 is N, and X1 and X2 are CH; or CD.

In one embodiment of the present specification, Formula 1 is represented by Formula 1-1 below.

[Formula 1-1]

In Formula 1-1, the definitions of L1, L2, Ar1 and Ar2 are the same as those defined in Formula 1, and the portion of the benzene ring with no substituent is substituted with H or D.

In one embodiment of the present specification, Chemical Formula 1 is represented by Chemical Formulas 2-1 and 2-2 below.

[Formula 2-1]

[Formula 2-2]

In Chemical Formulas 2-1 and 2-2, L1, L2, Ar1 and Ar2 are defined as defined in Chemical Formula 1, and the portion where no substituent is displayed on the benzene ring is substituted with H or D.

In one embodiment of the present specification, Chemical Formula 1 is represented by Chemical Formulas 3-1 and 3-2 below.

[Formula 3-1]

[Formula 3-2]

In Chemical Formulas 3-1 and 3-2, L1, L2, Ar1, and Ar2 are defined as defined in Chemical Formula 1, and the portion of the benzene ring with no substituent is substituted with H or D.

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

A compound according to an exemplary embodiment of the present specification may be prepared by a manufacturing method described below. If necessary, substituents may be added or excluded, and the position of substituents may be changed. In addition, based on techniques known in the art, starting materials, reactants, reaction conditions, and the like can be changed.

The compound represented by Chemical Formula 1 containing deuterium can be prepared by a known deuteration reaction. According to an exemplary embodiment of the present specification, the compound of Formula 1 may be formed using a deuterated compound as a precursor, or deuterium may be introduced into the compound through a hydrogen-deuterium exchange reaction using a deuterated solvent under an acid catalyst. there is.

In the present specification, compounds having various energy band gaps may be synthesized by introducing various substituents into the core structure of the compound represented by Formula 1. 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 above structure.

In addition, the present specification provides an organic light emitting device including the aforementioned compound.

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

In this specification, when a part is said to "include" a certain component, it means that it may further include other components without excluding other components unless otherwise stated.

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

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

The compound 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 means spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.

The organic material layer of the organic light emitting device of the present specification may have a single-layer structure, or 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 includes 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. may have a structure that includes However, the structure of the organic light emitting device of the present specification is not limited thereto and may include fewer or more organic material layers.

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

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 hole injection layer may include the compound represented by Chemical Formula 1.

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

In one embodiment of the present specification, the organic material layer includes an electron transport layer, an electron injection layer, an electron transport and injection layer, or a hole blocking layer, and the electron transport layer, electron injection layer, electron transport and injection layer, or hole blocking layer It may include the compound represented by Formula 1 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-described formula (1) compounds may be included.

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

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 Formula 1 above.

In one 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 20 Å to 1500 Å.

In one 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 one 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 as a host.

In one 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 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 Chemical Formula 1 described above.

In the organic light emitting device according to one embodiment of the present specification, the light emitting layer further includes a fluorescent dopant or a phosphorescent dopant. At this time, the dopant in the light emitting layer is included in 1 part by weight to 50 parts by weight based on 100 parts by weight of the host.

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

In one 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 one or more organic material layers 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 transport and injection layer. can

In one 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 Chemical Formula 1.

In one embodiment of the present specification, the two or more organic material layers may be two or more 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 one embodiment of the present specification, the two or more organic material layers may be two or more 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 one 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 Chemical Formula 1. Specifically, in one embodiment of the present specification, the compound represented by Formula 1 may be included in one layer 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 one 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 containing 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, and for example, a metal or a metal complex may be used.

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

In one 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 Chemical Formula 1. Specifically, in one embodiment of the present specification, the compound represented by Chemical Formula 1 may be included in one of the two or more hole transport layers, and may be included in each of the two or more hole transport layers.

In addition, in one 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. there is.

In one embodiment of the present specification, the organic material layer further comprises a hole injection layer or a hole transport layer containing a compound containing an arylamine group, a carbazolyl group, or a benzocarbazolyl group in addition to the organic material layer containing the compound represented by Formula 1 can include

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

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

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/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/emission 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.

2 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, and an electron transport layer 8 , shows an example of an organic light emitting device in which an electron injection layer 9 and a cathode 10 are sequentially stacked. In such a 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) can be included. In this structure, the compound may preferably be included in the hole blocking layer (7).

Figure 3 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 and injection layer 11 and a cathode 10 are sequentially stacked. In this structure, the compound is applied to the hole injection layer 3, the hole transport layer 4, the electron blocking layer 5, the light emitting layer 6, the hole blocking layer 7 or the electron transport and injection layer 11. can be included In this structure, the compound may preferably be included in the hole blocking layer (7).

In one embodiment of the present specification, the electron blocking layer and the light emitting layer may be provided adjacently. 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 with each other.

The organic light emitting device of the present specification may be manufactured with materials and methods known in the art, except that at least one layer of organic material layers includes the compound, that is, the compound represented by Chemical 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 according to the present specification uses a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to form a metal or conductive metal oxide or an alloy thereof on a substrate. It is prepared by depositing an anode, forming 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 thereon, and then depositing a material that can be used as a cathode thereon. It 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 at least one 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 transport and injection layer.

The organic material layer may have a multi-layer structure including a hole transport layer, a hole injection layer, a hole transport and injection layer, an electron blocking layer, a light emitting layer and an electron transport layer, an electron injection layer, and an electron transport and injection layer, but is not limited thereto and has a single layer structure. can be In addition, the organic material layer can be formed by a solvent process other than a deposition method using various polymer materials, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or a thermal transfer method. Can be made in layers.

The anode is an electrode for injecting holes, and the anode material is preferably a material having a high 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, and gold or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO: Al or SnO ₂ : 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 it is preferable that the cathode material is a material having a small work function so as to easily inject electrons 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; There are multi-layered materials such as LiF/Al or LiO ₂ /Al, but are not limited thereto.

The hole injection layer is a layer that serves to facilitate the injection of holes from the anode to the light emitting layer, and the hole injection material is a material that can receive holes well from the anode at a low voltage, HOMO (highest occupied) of the hole injection material molecular orbital) is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrilehexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene-based organic materials. of organic materials, anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited thereto. The hole injection layer may have a thickness of 1 nm to 150 nm. If the thickness of the hole injection layer is 1 nm or more, there is an advantage in preventing the hole injection characteristics from deteriorating, and if the thickness is 150 nm or less, the thickness of the hole injection layer is too thick, so that a driving voltage is required to improve hole movement. There are advantages to preventing it from rising.

The hole transport layer may play a role of facilitating hole transport. As the hole transport material, a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer and having high hole mobility is suitable. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated parts.

A hole buffer layer may be additionally provided between the hole injection layer and the hole transport layer, and may include a hole injection or transport material known in the art.

An electron blocking layer may be provided between the hole transport layer and the light emitting layer. The above-mentioned compounds or materials known in the art may be used for the electron blocking layer.

The light emitting layer may emit red, green or blue light and may be made 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-hydroxybenzoquinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; Polyfluorene, rubrene, etc., but are not limited thereto.

A host material for the light emitting layer includes a condensed aromatic ring derivative or a compound containing a hetero ring. 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, etc., but are not limited thereto.

When the light emitting layer emits red light, PIQIr (acac) (bis (1-phenylisoquinoline) acetylacetonateiridium), PQIr (acac) (bis (1-phenylquinoline) acetylacetonate iridium), PQIr (tris (1-phenylquinoline) iridium) are used as light emitting dopants. ), a phosphorescent material such as octaethylporphyrin platinum (PtOEP), or a fluorescent material such as Alq ₃ (tris(8-hydroxyquinolino)aluminum), but is not limited thereto. When the light emitting layer emits green light, a phosphorescent material 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 light emitting dopant. However, it is not limited thereto. When the light emitting layer emits blue light, as the light emitting dopant, a phosphorescent material such as (4,6-F2ppy) ₂ Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), distryarylene (DSA), Fluorescent materials such as PFO-based polymers and PPV-based polymers may be used, but are not limited thereto.

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

The electron transport layer may serve to facilitate electron transport. As the electron transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable. Specific examples include Al complexes of the aforementioned compounds or 8-hydroxyquinoline; Complexes containing Alq ₃ ; organic radical compounds; hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport layer may have a thickness of 1 nm to 50 nm. If the thickness of the electron transport layer is 1 nm or more, there is an advantage in preventing deterioration in electron transport properties, and if it is 50 nm or less, the thickness of the electron transport layer is too thick to prevent the increase in driving voltage to improve electron movement. There are benefits to avoiding it.

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

According to an exemplary embodiment of the present invention, the organic light emitting device includes an electron transport and injection layer, and materials for the electron transport layer and electron injection layer described above may be used.

The electron transport and injection layer may include a triazine-based compound and lithium quinolate in a weight ratio of 2:1 to 1:2.

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)( There are o-cresolato) gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, and bis(2-methyl-8-quinolinato)(2-naphtolato)gallium. Not limited to this.

The hole blocking layer is a layer that blocks 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 complexes, and the like, but are not limited thereto.

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

The organic light emitting device according to the present specification may be included in and used 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 described in detail in order to specifically describe the present specification. However, the embodiments according to the present specification may be modified in many different forms, and the scope of the present application is not construed as being limited to the embodiments detailed below. The embodiments of the present application are provided to more completely explain the present specification to those skilled in the art.

<Production Example 1>

Synthesis of Compound 1

After completely dissolving the compounds 1-bromo-4-(phenylsulfonyl)benzene (7.50g, 25.24 mmol) and a-1 (13.18, 30.29 mmol) in 240ml of tetrahydrofuran in a 500ml round bottom flask under a nitrogen atmosphere, 2M potassium carbonate aqueous solution ( 120ml) was added, and after adding tetrakis-(triphenylphosphine)palladium (1.46g, 1.26 mmol), the mixture was heated and stirred for 6 hours. After lowering the temperature to room temperature, removing the water layer, drying with anhydrous magnesium sulfate, concentrating under reduced pressure, and recrystallizing with 210ml of ethyl acetate to prepare compound 1 (8.11g, 61%).

MS[M+H] ⁺ = 526

<Production Example 2>

Synthesis of compound 2

After completely dissolving compound 1-bromo-4-(phenylsulfonyl)benzene (7.50 g, 25.24 mmol) and compound a-2 (15.48 g, 30.29 mmol) in 240 mL of tetrahydrofuran in a 500 mL round bottom flask under a nitrogen atmosphere, After adding 2M potassium carbonate aqueous solution (120 mL), tetrakis-(triphenylphosphine)palladium (1.46 g, 1.26 mmol) was added, and the mixture was heated and stirred for 4 hours. After lowering the temperature to room temperature, removing the water layer, drying with anhydrous magnesium sulfate, concentrating under reduced pressure, and recrystallizing with 240 ml of ethyl acetate to prepare Compound 2 (9.57 g, 63%).

MS[M+H] ⁺ = 602

<Production Example 3>

Synthesis of compound 3

After completely dissolving compound 1-bromo-4-(phenylsulfonyl)benzene (7.50 g, 25.24 mmol) and compound a-3 (17.78 g, 30.29 mmol) in 240 mL of tetrahydrofuran in a 500 mL round bottom flask in a nitrogen atmosphere, After adding 2M potassium carbonate aqueous solution (120 mL), tetrakis-(triphenylphosphine)palladium (1.46 g, 1.26 mmol) was added, and the mixture was heated and stirred for 6 hours. After lowering the temperature to room temperature, removing the water layer, drying with anhydrous magnesium sulfate, concentrating under reduced pressure, and recrystallizing with 250 ml of ethyl acetate to prepare compound 3 (11.34 g, 66%).

MS[M+H] ⁺ = 678

<Production Example 4>

Synthesis of compound 4

After completely dissolving compound 1-bromo-4-(phenylsulfonyl)benzene (7.50 g, 25.24 mmol) and compound a-4 (17.72 g, 30.29 mmol) in 240 mL of tetrahydrofuran in a 500 mL round bottom flask in a nitrogen atmosphere, After adding 2M potassium carbonate aqueous solution (120 mL), tetrakis-(triphenylphosphine)palladium (1.46 g, 1.26 mmol) was added, and the mixture was heated and stirred for 6 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 250 ml of ethyl acetate to prepare compound 4 (12.27 g, 72%).

MS[M+H] ⁺ = 676

<Production Example 5>

Synthesis of compound 5

After completely dissolving compound 1-bromo-4-(phenylsulfonyl)benzene (7.50 g, 25.24 mmol) and compound a-5 (17.87 g, 30.29 mmol) in 240 mL of tetrahydrofuran in a 500 mL round bottom flask under a nitrogen atmosphere. After adding 2M potassium carbonate aqueous solution (120 mL), tetrakis-(triphenylphosphine)palladium (1.46 g, 1.26 mmol) was added, and the mixture was heated and stirred for 8 hours. After lowering the temperature to room temperature, removing the water layer, drying with anhydrous magnesium sulfate, concentrating under reduced pressure, and recrystallizing with 280 mL of ethyl acetate to prepare compound 5 (10.97 g, 64%).

MS[M+H] ⁺ = 681

<Production Example 6>

Synthesis of compound 6

After completely dissolving the compounds 1-bromo-4-(phenylsulfonyl)benzene (7.50 g, 25.24 mmol) and a-6 (18.50 g, 30.29 mmol) in 240 ml of tetrahydrofuran in a 500 ml round-bottom flask under a nitrogen atmosphere, 2M potassium carbonate aqueous solution (120ml) was added, and after adding tetrakis-(triphenylphosphine)palladium (1.46 g, 1.26 mmol), the mixture was heated and stirred for 5 hours. After lowering the temperature to room temperature, removing the water layer, drying with anhydrous magnesium sulfate, concentrating under reduced pressure, and recrystallizing with 290ml of ethyl acetate to prepare compound 6 (11.65 g, 66%).

MS[M+H] ⁺ = 702

<Production Example 7>

Synthesis of compound 7

After completely dissolving the compounds 1-bromo-4-(phenylsulfonyl)benzene (7.50 g, 25.24 mmol) and a-7 (15.90 g, 30.29 mmol) in 240 ml of tetrahydrofuran in a 500 ml round bottom flask under a nitrogen atmosphere, 2M potassium carbonate aqueous solution (120ml) was added, and after adding tetrakis-(triphenylphosphine)palladium (1.46 g, 1.26 mmol), the mixture was heated and stirred for 6 hours. After lowering the temperature to room temperature, removing the water layer, drying with anhydrous magnesium sulfate, concentrating under reduced pressure, and recrystallizing with 310 ml of ethyl acetate to prepare compound 7 (8.86 g, 57%).

MS[M+H] ⁺ = 616

<Production Example 8>

Synthesis of compound 8

After completely dissolving compound 1-bromo-4-(phenylsulfonyl)benzene (7.50 g, 25.24 mmol) and compound a-8 (16.38 g, 30.29 mmol) in 240 mL of tetrahydrofuran in a 500 mL round bottom flask under a nitrogen atmosphere, After adding 2M potassium carbonate aqueous solution (120 mL), tetrakis-(triphenylphosphine)palladium (1.46 g, 1.26 mmol) was added, and the mixture was heated and stirred for 6 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 270 mL of ethyl acetate to prepare Compound 8 (9.34 g, 59%).

MS[M+H] ⁺ = 632

<Production Example 9>

Synthesis of compound 9

After completely dissolving compound 1-bromo-4-(phenylsulfonyl)benzene (7.50 g, 25.24 mmol) and compound a-9 (15.45 g, 30.29 mmol) in 240 mL of tetrahydrofuran in a 500 mL round bottom flask in a nitrogen atmosphere, A 2M aqueous solution of potassium carbonate (120 mL) was added, and tetrakis-(triphenylphosphine)palladium (1.46 g, 1.26 mmol) was added thereto, followed by heating and stirring for 5 hours. After lowering the temperature to room temperature, removing the water layer, drying with anhydrous magnesium sulfate, concentrating under reduced pressure, and recrystallizing with 320 mL of ethyl acetate to prepare compound 9 (8.63 g, 57%).

MS[M+H] ⁺ = 601

<Production Example 10>

Synthesis of compound 10

After completely dissolving compound 1-bromo-4-(phenylsulfonyl)benzene (7.50 g, 25.24 mmol) and compound a-10 (18.53 g, 30.29 mmol) in 240 mL of tetrahydrofuran in a 500 mL round bottom flask in a nitrogen atmosphere, A 2M aqueous solution of potassium carbonate (120 mL) was added, and tetrakis-(triphenylphosphine)palladium (1.46 g, 1.26 mmol) was added thereto, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 320 mL of tetrahydrofuran to prepare Compound 10 (9.22 g, 51%).

MS[M+H] ⁺ = 718

<Production Example 11>

Synthesis of compound 11

After completely dissolving compound 1-bromo-4-(phenylsulfonyl)benzene (7.50 g, 25.24 mmol) and compound a-11 (19.99 g, 30.29 mmol) in 240 mL of tetrahydrofuran in a 500 mL round bottom flask in a nitrogen atmosphere, After adding 2M potassium carbonate aqueous solution (120 mL), tetrakis-(triphenylphosphine)palladium (1.46 g, 1.26 mmol) was added, and the mixture was heated and stirred for 7 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 290 mL of ethyl acetate to prepare Compound 11 (12.77 g, 66%).

MS[M+H] ⁺ = 766

<Production Example 12>

Synthesis of compound 12

After completely dissolving the compounds 1-bromo-4-(phenylsulfonyl)benzene (7.50 g, 25.24 mmol) and a-12 (17.51, 30.29 mmol) in 240 ml of tetrahydrofuran in a 500 ml round bottom flask under a nitrogen atmosphere, a 2 M aqueous solution of potassium carbonate ( 120ml) was added, and after adding tetrakis-(triphenylphosphine)palladium (1.46g, 1.26 mmol), the mixture was heated and stirred for 6 hours. After lowering the temperature to room temperature, removing the water layer, drying with anhydrous magnesium sulfate, concentrating under reduced pressure, and recrystallizing with 270ml of ethyl acetate to prepare compound 12 (13.11g, 77%).

MS[M+H] ⁺ = 677

<Production Example 13>

Synthesis of compound 13

After completely dissolving the compounds 1-bromo-4-(phenylsulfonyl)benzene (7.50 g, 25.24 mmol) and a-13 (17.47 g, 30.29 mmol) in 240 ml of tetrahydrofuran in a 500 ml round-bottom flask under a nitrogen atmosphere, 2M potassium carbonate aqueous solution (120ml) was added, and after adding tetrakis-(triphenylphosphine)palladium (1.46g, 1.26 mmol), the mixture was heated and stirred for 6 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 260ml of ethyl acetate to prepare compound 13 (9.12g, 75%).

MS[M+H] ⁺ = 676

Example 1-1

A glass substrate coated with ITO (indium tin oxide) to a thickness of 1,000 Å was put in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a Fischer Co. product was used as the detergent, and distilled water filtered through a second filter of a Millipore Co. product was used as the distilled water. After washing the ITO for 30 minutes, ultrasonic cleaning was performed twice with distilled water for 10 minutes. After washing with distilled water, ultrasonic cleaning was performed with solvents such as isopropyl alcohol, acetone, and methanol, dried, and transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transferred to a vacuum deposition machine.

A hole injection layer was formed by thermally vacuum-depositing the following compound HI1 and the following compound HI2 to a thickness of 100 Å in a ratio of 98:2 (molar ratio) on the ITO transparent electrode prepared as described above. A hole transport layer was formed by vacuum depositing a compound (1150 Å) represented by Chemical Formula HT1 on the hole injection layer. Subsequently, an electron blocking layer was formed by vacuum depositing a compound of EB1 to a film thickness of 50 Å on the hole transport layer. Subsequently, a light emitting layer was formed by vacuum depositing a compound represented by Chemical Formula BH and a compound represented by Chemical Formula BD at a weight ratio of 25:1 to a film thickness of 200 Å on the electron blocking layer. A hole blocking layer was formed by vacuum depositing a compound represented by Compound 1 synthesized in Preparation Example 1 to a film thickness of 50 Å on the light emitting layer. Subsequently, a compound represented by Chemical Formula ET1 and a compound represented by Chemical Formula LiQ were vacuum deposited at a weight ratio of 1:1 on the hole blocking layer to form an electron transport and injection layer with a thickness of 310 Å. A negative electrode 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 on the cathode was 0.3Å / sec, and the deposition rate of aluminum was 2Å / sec, and the vacuum level during deposition was 2ⅹ10 ^-7 ~ Maintaining 5x10 ^-6 torr, an organic light emitting device was manufactured.

Examples 1-2 to 1-13

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

Comparative Examples 1-1 to 1-6

An organic light emitting device was manufactured in the same manner as in Example 1-1, except that the compounds shown in Table 1 were used instead of the compounds of Preparation Example 1. The compounds of HB1, HB2, HB3, HB4, HB5, and HB6 used in Table 1 are as follows.

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

compound
(hole blocking layer) Voltage
(V@10mA
/cm ² ) efficiency
(cd/A@10mA
/cm ² ) color coordinates
(x,y) T95
(hr) Example 1-1 compound 1 4.35 6.48 (0.145, 0.146) 250 Example 1-2 compound 2 4.31 6.44 (0.145, 0.145) 285 Example 1-3 compound 3 4.33 6.39 (0.146, 0.145) 255 Example 1-4 compound 4 4.30 6.27 (0.146, 0.146) 280 Example 1-5 compound 5 4.35 6.22 (0.147, 0.146) 285 Example 1-6 compound 6 4.31 6.31 (0.145, 0.147) 255 Examples 1-7 compound 7 4.39 6.33 (0.146, 0.145) 250 Examples 1-8 compound 8 4.34 6.39 (0.147, 0.146) 285 Examples 1-9 compound 9 4.38 6.26 (0.145, 0.144) 250 Examples 1-10 compound 10 4.37 6.39 (0.146, 0.145) 275 Example 1-11 compound 11 4.33 6.37 (0.145, 0.147) 275 Examples 1-12 compound 12 4.31 6.21 (0.145, 0.146) 260 Comparative Example 1-1 HB1 4.64 5.85 (0.147, 0.145) 115 Comparative Example 1-2 HB2 4.72 5.60 (0.146, 0.145) 185 Comparative Example 1-3 HB3 4.81 5.93 (0.146, 0.147) 65 Comparative Example 1-4 HB4 4.97 6.04 (0.147, 0.146) 135 Comparative Example 1-5 HB5 5.09 5.77 (0.145, 0.145) 160 Comparative Example 1-6 HB6 4.84 5.91 (0.147, 0.147) 80

As shown in Table 1, the organic light emitting device using the compound of the present invention in which the ortho-oriented phenylene group is connected to sulfonyldibenzene and an N-containing monocyclic ring as a hole blocking layer has efficiency, driving voltage and stability aspects of the organic light emitting device. showed excellent properties.

Examples 1-1 to 1-12, compared to Comparative Examples 1-1, 1-2 and 1-4 using compounds in which sulfonyldibenzene and a meta or para-oriented phenylene group are connected to an N-containing monocyclic ring, lower voltage , it was found that high efficiency, especially long life characteristics were exhibited.

It can be seen that Examples 1-1 to 1-12 show characteristics of low voltage, high efficiency, and especially long life compared to Comparative Examples 1-3 and 1-6 using a compound in which sulfonyldibenzene and N-containing monocyclic ring are directly connected. could

Examples 1-1 to 1-12, compared to Comparative Example 1-5 using a compound having a structure in which three or more polycyclic rings are connected between sulfonyldibenzene and an N-containing monocyclic ring, have characteristics of low voltage, high efficiency, and especially long life. could see what

Although the preferred embodiment (hole blocking layer) of the present invention has been described above, the present invention is not limited thereto and can be modified and implemented in various ways within the scope of the claims and detailed description of the invention. belongs to the category of 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 (12)

A compound represented by Formula 1 below:
[Formula 1]

In Formula 1,
L1 and L2 are the same as or different from each other, and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; or a nitrile group
X1 to X3 are the same or different, and are each independently N; CH; or a CD;
At least one of X1 to X3 is N,
The part where no substituent is shown on the benzene ring is substituted with H or D. The compound according to claim 1, wherein Chemical Formula 1 is represented by the following Chemical Formula 1-1:
[Formula 1-1]

In Formula 1-1, definitions of L1, L2, Ar1, and Ar2 are the same as those defined in Formula 1, and a portion of the benzene ring with no substituent is substituted with H or D. The compound according to claim 1, wherein Chemical Formula 1 is represented by any one of the following Chemical Formulas 2-1 and 2-2:
[Formula 2-1]

[Formula 2-2]

In Chemical Formulas 2-1 and 2-2, L1, L2, Ar1 and Ar2 are defined as defined in Chemical Formula 1, and the portion where no substituent is displayed on the benzene ring is substituted with H or D. The compound according to claim 1, wherein Chemical Formula 1 is represented by any one of the following Chemical Formulas 3-1 and 3-2:
[Formula 3-1]

[Formula 3-2]

In Chemical Formulas 3-1 and 3-2, L1, L2, Ar1, and Ar2 are defined as defined in Chemical Formula 1, and the portion of the benzene ring with no substituent is substituted with H or D. The method according to claim 1, L1 and L2 are the same as or different from each other, and each independently a direct bond; or a compound selected from the following structures:

In the above structure,
The structure is substituted or unsubstituted with deuterium,
The dotted line is connected to Formula 1 above,
R11 and R12 are the same as or different from each other, and are each independently substituted or unsubstituted hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group. The method according to claim 1, Ar1 and Ar2 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 quaterphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted spirobifluorenyl group; A substituted or unsubstituted triphenylenyl group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted dibenzothiophene group; Or a compound that is a nitrile group. The method according to claim 1, L1 and L2 are the same as or different from each other, and each independently a direct bond; an arylene group having 6 to 30 carbon atoms unsubstituted or substituted with heavy hydrogen; Or an O or S-containing heteroarylene group having 2 to 30 carbon atoms unsubstituted or substituted with deuterium,
Ar1 and Ar2 are the same as or different from each other, and each independently represents a deuterium, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with a nitrile group; a heteroaryl group containing O or S having 2 to 30 carbon atoms unsubstituted or substituted with heavy hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a nitrile group; Or a compound that is a nitrile group. The compound according to claim 1, wherein Formula 1 is represented by any one of the following compounds:

. anode; cathode; and one or more organic material layers provided between the anode and the cathode, wherein at least one of the organic material layers includes the compound according to any one of claims 1 to 8. The method of claim 9,
wherein the organic material layer includes a light emitting layer, and the light emitting layer includes the compound. The method of claim 9,
The organic material layer includes an electron transport layer, an electron injection layer, or an electron transport and injection layer, wherein the electron transport layer, the electron injection layer, or the electron transport and injection layer includes the compound. The method of claim 9,
wherein the organic material layer includes a hole blocking layer, and the hole blocking layer includes the compound.

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