KR20210021762A - 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 comprising 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 can improve efficiency, low driving voltage, and/or lifespan characteristics in the organic light emitting device.

Description

A compound and an organic light-emitting device comprising the same TECHNICAL FIELD

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

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

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

Korean Patent Publication No. 10-2016-0142909

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 the following formula (1).

[Formula 1]

In Formula 1,

X is SO ₂ ,

Two of R1 to R8 are represented by the following formula A, and the rest not represented by formula A are hydrogen or deuterium,

At this time, R2 and R7 of R1 to R8 are not formula A at the same time,

[Formula A]

In Formula A,

Ar is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In addition, according to an exemplary embodiment of the present specification, the first electrode; A second electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound represented by Formula 1 above. Provides.

The compound described herein 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 may improve efficiency, low driving voltage, and/or improve lifespan characteristics in an organic light-emitting device. In particular, the compounds described in the present specification may be used as hole injection, hole transport, hole injection and hole transport, electron blocking, light emission, hole blocking, electron transport, or electron injection material. In addition, compared to the existing organic light emitting device, there is an effect of a low driving voltage, high efficiency or long life.

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

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

는 결합위치를 의미한다.In this specification,

Means the bonding position.

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

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

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

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

In the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; Nitrile group; Nitro group; Hydroxy group; Amino group; Silyl group; Boron group; Alkoxy group; Aryloxy group; Alkyl group; Cycloalkyl group; Aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, two or more of the substituents exemplified above are substituted with a connected substituent, or does not have any substituents. For example, "a substituent to which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are connected.

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 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, etc., but is not limited thereto. 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. The boron group specifically includes a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, and a phenyl boron group, but is not limited thereto.

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 alkyl group has 1 to 30 carbon atoms. 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, and the like, but are not limited thereto.

In the present specification, the description of the above 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 the number of carbon atoms of the alkoxy group is not particularly limited, it is preferably 1 to 20 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, and the like, but are not limited thereto.

Substituents including an alkyl group, an alkoxy group, and other alkyl group moieties described in the present specification include all of a straight chain or a branched form.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably 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 cycloalkyl group has 3 to 20 carbon atoms. 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 are not limited thereto.

In the present specification, the amine group is -NH ₂ , and the above-described alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, and combinations thereof may be substituted for the amine group. 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 amine group has 1 to 20 carbon atoms. According to an exemplary embodiment, the amine group has 1 to 10 carbon atoms. 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, Although there are a ditolylamine group, a phenyltolylamine group, a diphenylamine group, etc., it is not limited to these.

In the present specification, the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, a terphenyl group, or a quarterphenyl 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 triphenyl group, a chrysenyl group, a fluorenyl group, a triphenylenyl group, and the like, but is limited thereto. no.

In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.

,

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 described above with respect to the aryl 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 hetero atoms, and the number of carbons is not particularly limited, but is preferably 2 to 60 carbon atoms. According to an exemplary embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. Examples of the heterocyclic group include pyridine group, pyrrole group, pyrimidine group, quinoline group, pyridazinyl group, furan group, thiophene group, imidazole group, pyrazole group, dibenzofuran group, dibenzothiophene group , Carbazole group, benzocarbazole group, naphthobenzofuran group, benzonaphthothiophene group, indenocarbazole group, triazinyl group, and the like, but are not limited thereto.

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

In the present specification, in a substituted or unsubstituted ring formed by bonding with adjacent groups to each other, "ring" is a hydrocarbon ring; Or a hetero ring.

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

In the present specification, the meaning of forming a ring by bonding with adjacent groups to each other 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 of these. The hydrocarbon ring means a ring consisting only of carbon and hydrogen atoms. The heterocycle refers to a ring including at least one selected from N, O, P, S, Si and Se. In the present specification, the aliphatic hydrocarbon ring, the aromatic hydrocarbon ring, the aliphatic hetero ring and the aromatic hetero ring may be monocyclic or polycyclic.

In the present specification, the aliphatic hydrocarbon ring refers to a ring that is not aromatic and includes only carbon and hydrogen atoms. Examples of aliphatic hydrocarbon rings include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, and the like, It is not limited to this.

In the present specification, the aromatic hydrocarbon ring means an aromatic ring consisting only of 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, the aromatic hydrocarbon ring may be interpreted as having the same meaning as an aryl group.

In the present specification, the 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, oxephan, and azocaine , Thiocane, and the like, but are not limited thereto.

In the present specification, the aromatic heterocycle means an aromatic ring containing at least one heteroatom. 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, dryazainden, indole, indolizine, benzothiazole, benzoxazole, benzoimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzo Carbazole, dibenzocarbazole, phenazine, imidazopyridine, phenoxazine, indolocarbazole, indenocarbazole, and the like, but are not limited thereto.

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

The present specification provides a compound represented by the following formula (1).

중 3,7을 제외한 위치에 안트라센이 연결된다. 이때, 하기 화합물은 구조 내에 디벤조티오펜디옥사이드을 포함함으로써 우수한 전하 밸런스(Charge balance) 특성을 나타낸다.The compound represented by the following formula 1 is a compound in which anthracene is bonded to dibenzothiophene dioxide, and the bonding position of dibenzothiophene dioxide

Anthracene is connected to positions other than 3 and 7 of the above. At this time, the following compounds exhibit excellent charge balance characteristics by including dibenzothiophene dioxide in the structure.

When the compound represented by the following formula (1) is used in the organic material layer of the organic light-emitting device, the efficiency of the organic light-emitting device is improved, as well as a low driving voltage and excellent lifespan characteristics.

Hereinafter, Formula 1 will be described in detail.

[Formula 1]

In Formula 1,

X is SO ₂ ,

Two of R1 to R8 are represented by the following formula A, and the rest not represented by formula A are hydrogen or deuterium,

At this time, R2 and R7 of R1 to R8 are not formula A at the same time,

[Formula A]

In Formula A,

Ar is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

According to an exemplary embodiment of the present specification, of R1 to R8, R1 and R5 are represented by Formula A, and the rest are hydrogen or deuterium.

According to an exemplary embodiment of the present specification, of R1 to R8, R1 and R6 are represented by Formula A, and the rest are hydrogen or deuterium.

According to an exemplary embodiment of the present specification, of R1 to R8, R1 and R7 are represented by Formula A, and the rest are hydrogen or deuterium.

According to an exemplary embodiment of the present specification, of R1 to R8, R1 and R8 are represented by Formula A, and the rest are hydrogen or deuterium.

According to an exemplary embodiment of the present specification, of R1 to R8, R2 and R5 are represented by Formula A, and the rest are hydrogen or deuterium.

According to an exemplary embodiment of the present specification, of R1 to R8, R2 and R6 are represented by Formula A, and the rest are hydrogen or deuterium.

According to an exemplary embodiment of the present specification, of R1 to R8, R3 and R5 are represented by Formula A, and the rest are hydrogen or deuterium.

According to an exemplary embodiment of the present specification, of R1 to R8, R3 and R6 are represented by Formula A, and the rest are hydrogen or deuterium.

According to an exemplary embodiment of the present specification, of R1 to R8, R4 and R5 are represented by Formula A, and the rest are hydrogen or deuterium.

According to an exemplary embodiment of the present specification, R1 and R5 of R1 to R8; R1 and R6; R1 and R7; R1 and R8; R2 and R5; R2 and R6; R3 and R5; R3 and R6; Or any one pair of R4 and R5 is represented by the following formula A, and the remainder is hydrogen.

According to an exemplary embodiment of the present specification, R2 and R7 of R1 to R8 are not Formula A at the same time.

According to an exemplary embodiment of the present specification, in Chemical Formula 1, Chemical Formula A is asymmetrically bonded to both benzene rings based on X. That is, R1, R8; R2, R7; R3, R6; And at the positions of R4 and R5, formula A is not bonded at the same time.

According to an exemplary embodiment of the present specification, Ar is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; It is a substituted or unsubstituted C2-C30 heterocyclic group.

According to an exemplary embodiment of the present specification, Ar is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; It is a substituted or unsubstituted C2 to C20 heterocyclic group.

According to an exemplary embodiment of the present specification, Ar is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms; It is a substituted or unsubstituted C2-C15 heterocyclic group.

According to an exemplary embodiment of the present specification, Ar is a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; It is a substituted or unsubstituted C2 to C10 heterocyclic group.

According to an exemplary embodiment of the present specification, Ar is 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 anthracenyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted triphenylenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.

According to an exemplary embodiment of the present specification, Ar is 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 anthracenyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted triphenylenyl group; It is a substituted or unsubstituted fluorenyl group.

According to an exemplary embodiment of the present specification, Ar is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; It is a substituted or unsubstituted naphthyl group.

According to an exemplary embodiment of the present specification, Formula 1 may be represented by any one of Formulas 1-1 to 1-9 below.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

[Formula 1-7]

[Formula 1-8]

[Formula 1-9]

In Formulas 1-1 to 1-9,

X is SO ₂ ,

Ar1 and Ar2 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.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; It is a substituted or unsubstituted C2-C30 heterocyclic group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; It is a substituted or unsubstituted C2 to C20 heterocyclic group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 12 carbon atoms; It is a substituted or unsubstituted C2-C15 heterocyclic group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; It is a substituted or unsubstituted C2 to C10 heterocyclic group.

According to an exemplary 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 anthracenyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted triphenylenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.

According to an exemplary 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 anthracenyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted triphenylenyl group; Or a substituted or unsubstituted fluorenyl group.

According to an exemplary 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; Or a substituted or unsubstituted naphthyl group.

According to an exemplary 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; Or a naphthyl group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as each other.

According to an exemplary embodiment of the present specification, Formula 1 may be represented by any one of the following structural formulas.

In the present invention, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure as described above. In addition, in the present invention, the HOMO and LUMO energy levels of the compound can be adjusted by introducing various substituents to the core structure of the above structure.

The compound of Formula 1 of the present invention may have a core structure as shown in the following scheme. Substituents may be bonded by methods known in the art, and the type, position, and number of substituents may be changed according to techniques known in the art.

<General Formula 1>

In General Formula 1, X and Ar are the same as defined in Formula 1.

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

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

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

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 specifically stated to the contrary.

The organic material layer of the organic light emitting device of the present specification may have a single-layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, as a representative example of the organic light emitting device of the present specification, the organic light emitting device may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, etc. as an organic material layer. have. However, the structure of the organic light emitting device is not limited thereto, and may include a smaller number of organic material layers.

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 above.

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

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 host, and further includes a dopant.

In the exemplary embodiment of the present specification, the emission layer includes a host and a dopant, the host includes the compound, and the dopant is a phosphorescent dopant or a fluorescent dopant.

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.

In the exemplary embodiment of the present specification, when the light emitting layer includes a host and a dopant, the content of the dopant may be included in an amount of 0.1 parts by weight to 50 parts by weight based on 100 parts by weight of the host, and preferably 1 part by weight to 30 parts by weight. It can be included as a wealth.

In the exemplary embodiment of the present specification, the fluorescent dopant may be selected from the following structures, but is not limited thereto.

In an exemplary embodiment of the present specification, an Ir complex may be used as the phosphorescent dopant, and for example, any one of the following structures may be used, but the present invention is not limited thereto.

In the exemplary embodiment of the present specification, the organic light-emitting device further includes one or more light-emitting layers. Each of the one or more emission layers may include the above-described fluorescent dopant or phosphorescent dopant.

According to an exemplary embodiment of the present specification, the organic light-emitting device includes two or more light-emitting layers, one of the two or more light-emitting layers includes a fluorescent dopant, and the other layer includes a phosphorescent dopant.

In an exemplary embodiment of the present specification, the compound represented by Formula 1 is included in an amount of 50 parts by weight or more and less than 100 parts by weight, more preferably 70 parts by weight or more and 99 parts by weight or less, based on 100 parts by weight of the total weight of the light emitting layer.

In the exemplary embodiment of the present specification, the emission layer may further include an additional host material, and the host may include a condensed aromatic ring derivative or a heterocyclic-containing compound. Specifically, condensed aromatic ring derivatives include pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds in addition to anthracene derivatives, and heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, triazine derivatives, and the like, and may be a mixture of two or more thereof, but are not limited thereto.

In the exemplary embodiment 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 comprises a compound represented by Formula 1 above. Includes.

In the exemplary embodiment of the present specification, the organic material layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the layer simultaneously injecting and transporting electrons is represented by Formula 1 above. Contains compounds.

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

In the 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 exemplary embodiment of the present specification, the organic material layer is a hole injection layer and a hole transport layer. It further includes one or two or more layers selected from the group consisting of a light-emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer.

In the exemplary embodiment of the present specification, the organic light emitting device includes a first electrode; A second electrode; A light emitting layer provided between the first electrode and the second electrode; And two or more organic material layers provided between the light-emitting layer and the first electrode, or between the light-emitting layer and the second electrode, and at least one of the two or more organic material layers includes a compound represented by Formula 1 above.

In the 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 layer for simultaneously transporting and injecting holes, and an electron 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 a compound represented by Formula 1 above. Specifically, in the 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 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, the electron transport layer may further include an n-type dopant. As the n-type dopant, those known in the art may be used, for example, a metal or a metal complex. For example, the electron transport layer including the compound represented by Formula 1 may further include LiQ (Lithium Quinolate).

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

In addition, in the 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 the exemplary embodiment of the present specification, the organic material layer further 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 Can include.

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

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

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.

For example, the structure of an organic light-emitting device according to an exemplary embodiment of the present specification is illustrated in FIGS. 1 and 2. 1 and 2 illustrate an organic light-emitting device and are not limited thereto.

1 illustrates a structure of an organic light-emitting device in which a substrate 1, an anode 2, an emission layer 3, and a cathode 4 are sequentially stacked. In such a structure, the compound may be included in the emission layer 3.

2 shows a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (8), an electron blocking layer (9), a light emitting layer (3), a hole blocking layer (6), an electron injection and transport layer ( 7) and a cathode 4 are shown in an example of an organic light-emitting device sequentially stacked. In such a structure, the compound is one of the hole injection layer (5), the hole transport layer (8), the electron blocking layer (9), the light emitting layer (3), the hole blocking layer (6), and the electron injection and transport layer (7). It can be included above the layer

The organic light emitting device of the present specification may be manufactured by materials and methods known in the art, except that at least one of the organic material layers includes the 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 of the present specification may be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, a metal or a conductive metal oxide or an alloy thereof is deposited on the substrate to form an anode. It can be manufactured by forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. 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.

In addition, the compound represented by Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.

In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate. However, the manufacturing method is not limited thereto.

As the anode material, a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer. For example, 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); A combination of a metal and an oxide such as ZnO:Al or SnO _{2 :Sb;} Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, but are not limited thereto.

The cathode material is generally preferably a material having a small work function so that electrons can be easily injected into the organic material layer. Metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; There are a multi-layered material such as LiF/Al or LiO _{2 /Al, but are not limited thereto.}

The light emitting layer may include an additional host material and a dopant material. Examples of the host material include condensed aromatic ring derivatives or heterocyclic-containing compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include dibenzofuran derivatives, ladder furan compounds, And pyrimidine derivatives, but are not limited thereto.

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

In the present specification, when the compound represented by Formula 1 is included in an organic material layer other than the emission layer or an additional emission layer is provided, the emission material of the emission layer is formed by transporting and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively. As a material capable of emitting light in the visible region, a material having good quantum efficiency for fluorescence or phosphorescence is preferable. For example, 8-hydroxy-quinoline aluminum complex (Alq3); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole, and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene; And rubrene, but are not limited thereto.

The hole injection layer is a layer for injecting holes from an electrode. It is preferable that the hole injection material has an ability to transport holes and thus has a hole injection effect at the anode and an excellent hole injection effect on the light emitting layer or the light emitting material. In addition, a material having excellent ability to prevent movement of excitons generated in the light emitting layer to the electron injection layer or the electron injection material is preferable. In addition, a material excellent in thin film formation ability is preferred. In addition, it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is 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 porphyrin, oligothiophene, arylamine-based organic material; Carbazole-based organic matter; Nitrile-based organics; Hexanitrile hexaazatriphenylene-based organic material; Quinacridone series organic matter; Perylene-based organics; Polythiophene-based conductive polymers such as anthraquinone and polyaniline, or a mixture of two or more of the above examples, but are not limited thereto.

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

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. The electron transport material is a material capable of receiving electrons from the cathode and transferring them to the light emitting layer, and a material having high mobility for electrons is preferable. Specific examples include Al complex of 8-hydroxyquinoline; Complexes including Alq3; Organic radical compounds; Hydroxyflavone-metal complex; Triazine derivatives; LiQ and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material, as used according to the prior art. In particular, suitable cathode materials are conventional materials that have a low work function and are followed by an aluminum layer or a silver layer. Specifically, there are cesium, barium, calcium, ytterbium and samarium, and in each case, an aluminum layer or a silver layer follows.

The electron injection layer is a layer that injects electrons from an electrode. It is preferable that the electron injection material is excellent in the ability to transport electrons, and has an electron injection effect from the second electrode and an excellent electron injection effect on the light-emitting layer or the light-emitting material. In addition, a material that prevents excitons generated in the light emitting layer from moving to the hole injection layer and has excellent thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, triazine, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. Derivatives thereof, metal complex compounds, and nitrogen-containing 5-membered ring derivatives, and mixtures of two or more of the above examples, but are not limited thereto.

As the metal complex compound, 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-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. , Is not limited thereto.

The electron blocking layer is a layer capable of improving the lifespan and efficiency of a device by preventing holes injected from the hole injection layer from entering the electron injection layer through the emission layer. Known materials may be used without limitation, and may be formed between the light-emitting layer and the hole injection layer, or between the light-emitting layer and a layer that simultaneously injects and transports holes.

The hole blocking layer is a layer that prevents 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, aluminum complexes, pyridine, pyrimidine, or triazine derivatives, but are not limited thereto.

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

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

The compound according to the present specification may act on a principle similar to that applied to an organic light-emitting device in an organic light-emitting device including an organic phosphorescent device, an organic solar cell, an organic photoreceptor, and an organic transistor. For example, the organic solar cell may have a structure including a negative electrode, a positive electrode, and a photoactive layer provided between the negative electrode and the positive electrode, and the photoactive layer may include the compound.

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

Manufacturing Example 1

Compound A (4.99 g, 10.67 mmol) and compound a1 (6.44 g, 19.34 mmol) were completely dissolved in 240 mL of tetrahydrofuran in a 500 mL round-bottom flask in a nitrogen atmosphere, and then 2M aqueous potassium carbonate solution (120 mL) was added thereto. , Tetrakis-(triphenylphosphine)palladium (0.67 g, 0.58 mmol) was added, 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 ethyl acetate 270 mL to prepare compound 1 (9.17 g, 66%).

MS[M+H] ⁺ = 721

Manufacturing Example 2

Compound B (4.27 g, 9.11 mmol) and compound a2 (6.33 g, 16.57 mmol) were completely dissolved in 240 mL of tetrahydrofuran in a 500 mL round-bottom flask in a nitrogen atmosphere, and then 2M aqueous potassium carbonate solution (120 mL) was added thereto. , Tetrakis-(triphenylphosphine)palladium (0.57 g, 0.50 mmol) was added, followed by heating and stirring for 4 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 2 (8.47 g, 58%).

MS[M+H] ⁺ = 822

Manufacturing Example 3

Compound C (5.39g, 11.51mmol) and compound a3 (7.33 g, 19.19 mmol) were completely dissolved in 280 mL of tetrahydrofuran in a 500 mL round-bottom flask in a nitrogen atmosphere, and then 2M aqueous potassium carbonate solution (140 mL) was added thereto. , Tetrakis-(triphenylphosphine)palladium (0.67 g, 0.58 mmol) was added, followed by heating and stirring for 4 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 230 mL of tetrahydrofuran to prepare compound 3 (10.19 g, 60%).

MS[M+H]+= 882

Manufacturing Example 4

Compound D (6.87 g, 14.67 mmol) and compound a1 (8.12 g, 24.46 mmol) were completely dissolved in 200 mL of tetrahydrofuran in a 500 mL round bottom flask in a nitrogen atmosphere, and then 2M aqueous potassium carbonate solution (100 mL) was added. , Tetrakis-(triphenylphosphine)palladium (0.85 g, 0.73 mmol) was added, followed by heating and stirring for 3 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 ethyl acetate to prepare compound 4 (9.74 g, 55%).

MS[M+H]+= 721

Manufacturing Example 5

Compound E (5.49 g, 11.73 mmol) and compound a2 (7.47 g, 19.55 mmol) were completely dissolved in 220 mL of xylene in a 500 mL round-bottom flask in a nitrogen atmosphere, and NaOtBu (2.82 g, 29.33 mmol) was added. After addition, bis (tri-tert-butylphosphine) palladium (0) (Bis (tri-tert-butylphosphine) palladium (0)) (0.68 g, 0.59 mmol) was added, followed by heating and stirring for 4 hours. After lowering the temperature to room temperature and removing the base by filtering, xylene was concentrated under reduced pressure and recrystallized with ethyl acetate 260 mL to prepare compound 5 (10.24 g, yield: 64%).

MS[M+H] ⁺ = 822

Manufacturing Example 6

Compound F (6.20 g, 13.26 mmol) and compound a3 (8.44 g, 22.099 mmol) were completely dissolved in 230 mL of xylene in a 500 mL round bottom flask in a nitrogen atmosphere, and NaOtBu (3.18 g, 33.14 mmol) was added. After addition, Bis (tri- tert- butylphosphine) palladium (0) (0.77 g, 0.66 mmol) was added, followed by heating and stirring for 3 hours. After lowering the temperature to room temperature and removing the base by filtering, xylene was concentrated under reduced pressure and recrystallized with 230 mL of ethyl acetate to prepare compound 6 (12.23g, yield: 67%).

MS[M+H] ⁺ = 822

Example 1-1

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

On the thus prepared ITO transparent electrode, a compound represented by the following formula HAT was thermally vacuum deposited to a thickness of 100 Å to form a hole injection layer. A hole transport layer was formed by vacuum depositing a compound (1250Å) represented by the following formula HT1 on the hole injection layer. Subsequently, the electron blocking layer was formed by vacuum depositing the following formula EB1 with a film thickness of 150 Å on the hole transport layer. Subsequently, a light emitting layer was formed by vacuum depositing the previously prepared compound 1 and the compound represented by the following formula BD with a film thickness of 200 Å on the electron blocking layer at a weight ratio of 25:1. A hole blocking layer was formed by vacuum depositing a compound represented by the following formula HB1 with a film thickness of 50 Å on the emission layer. Subsequently, a compound represented by the following formula ET1 and a compound represented by the following formula LiQ were vacuum-deposited at a weight ratio of 1:1 on the hole blocking layer to form an electron injection and transport layer with a thickness of 310Å. Lithium fluoride (LiF) in a thickness of 12 Å and aluminum in a thickness of 1,000 Å were sequentially deposited on the electron injection and transport layer to form a negative electrode.

In the above process, the deposition rate of the organic material was maintained at 0.4 ~ 0.7Å/sec, the deposition rate of lithium fluoride at the negative electrode was 0.3Å/sec, and the deposition rate of aluminum was 2Å/sec, and the vacuum degree during deposition was 2x10 ^-7 ~ An organic light emitting device was manufactured by maintaining ^{5x10 -6 torr.}

Examples 1-2 to 1-6

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

Comparative Examples 1-1 to 1-5

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the compound shown in Table 1 below was used instead of the compound 1 of Example 1-1. The compounds of BH1 to BH5 used in Table 1 are as follows.

Experimental Example 1

When a current was applied to the organic light emitting device prepared in the above Examples and Comparative Examples, voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in Table 1 below. T95 refers to the time it takes for the luminance to decrease from the initial luminance (6000 nit) to 95%.

compound
(Host of the light-emitting layer) Voltage
(V@10mA
/cm ² ) efficiency
(cd/A@10mA
/cm ² ) Color coordinates
(x,y) T95
(hr) Example 1-1 Manufacturing Example 1 4.05 7.83 (0.139, 0.047) 270 Example 1-2 Manufacturing Example 2 4.14 7.76 (0.138, 0.046) 265 Example 1-3 Manufacturing Example 3 4.15 7.69 (0.138, 0.046) 255 Example 1-4 Manufacturing Example 4 4.09 7.85 (0.137, 0.047) 270 Example 1-5 Manufacturing Example 5 4.18 7.71 (0.138, 0.045) 255 Example 1-6 Manufacturing Example 6 4.17 7.62 (0.138, 0.046) 265 Example 1-7 Manufacturing Example 7 4.26 7.80 (0.137, 0.046) 250 Example 1-8 Manufacturing Example 8 4.24 7.84 (0.137, 0.045) 240 Example 1-9 Manufacturing Example 9 4.22 7.81 (0.138, 0.047) 240 Example 1-10 Manufacturing Example 10 4.23 7.83 (0.139, 0.045) 255 Example 1-11 Manufacturing Example 11 4.21 7.82 (0.138, 0.045) 255 Example 1-12 Manufacturing Example 12 4.20 7.86 (0.139, 0.047) 240 Comparative Example 1-1 BH1 4.91 6.61 (0.139, 0.046) 165 Comparative Example 1-2 BH2 4.80 6.63 (0.139, 0.045) 150 Comparative Example 1-3 BH3 4.83 6.64 (0.138, 0.045) 165 Comparative Example 1-4 BH4 5.44 5.66 (0.138, 0.045) 185 Comparative Example 1-5 BH5 6.27 4.67 (0.137, 0.046) 70

As shown in Table 1, the organic light-emitting device using the compound of the present invention as a host of the light-emitting layer exhibited excellent characteristics in terms of efficiency, driving voltage, and stability of the organic light-emitting device.

In particular, in the organic light emitting device using the compound of the present invention, anthracene is symmetrically connected to the 2,8 / 1,9 position of the bonding position of dibenzofuran or dibenzothiophene, or the 3,7 position of the dibenzothiophene dioxide Compared to an organic light-emitting device manufactured by using a compound of BH1 to BH3 or BH5 to which anthracene is symmetrically connected as a host of the emission layer, it exhibits characteristics of low voltage, high efficiency and long lifespan. In addition, the organic light-emitting device manufactured by using a BH4 compound in which arylene or alkylene is bonded instead of dibenzothiophene dioxide of the core structure as a host of the emission layer has a high driving voltage because the charge balance is broken. And showed low efficiency and low lifetime characteristics.

At this time, the bonding position of the core structure is indicated as follows.

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

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

Claims (11)

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

In Formula 1,
X is SO ₂ ,
Two of R1 to R8 are represented by the following formula A, and the rest not represented by formula A are hydrogen or deuterium,
At this time, R2 and R7 of R1 to R8 are not formula A at the same time
[Formula A]

In Formula A,
Ar is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group. The compound of claim 1, wherein Formula 1 is represented by any one of the following Formulas 1-1 to 1-9:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

[Formula 1-7]

[Formula 1-8]

[Formula 1-9]

In Formulas 1-1 to 1-9,
X is SO ₂ ,
Ar1 and Ar2 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. The method according to claim 1, wherein Ar is 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 anthracenyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted triphenylenyl 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,
R1 and R5 of R1 to R8; R1 and R6; R1 and R7; R1 and R8; R2 and R5; R2 and R6; R3 and R5; R3 and R6; Or any one pair of R4 and R5 is represented by the above formula A, and the remainder is hydrogen. The compound of claim 1, wherein Formula 1 is represented by any one of the following structural formulas:

. A first electrode; A second electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers contains the compound according to any one of claims 1 to 5 Light-emitting element. The method of claim 6,
The organic material layer includes an emission layer, and the emission layer includes the compound. The method of claim 7,
The light-emitting layer includes a host, and the host includes the compound. The method of claim 7,
The emission layer includes a host and a dopant, the host includes the compound, and the dopant is a phosphorescent dopant or a fluorescent dopant. The method of claim 6,
The organic material layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer includes the compound. The method of claim 6,
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 comprises the compound.

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