KR20210042037A - 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 including the same. An exemplary embodiment of the present specification provides the compound represented by the chemical formula 1. The compound described herein can be used as a material for an organic material layer of the organic light emitting device.

Description

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

This application claims the benefit of the filing date of the Korean Patent Application No. 10-2019-0124692 filed with the Korean Intellectual Property Office on October 8, 2019, the entire contents of which are incorporated herein.

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

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

KR 10-2012-0116282 A

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,

L2 is a direct bond; A substituted or unsubstituted alkylene group; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Ar21 is a substituted or unsubstituted aryl group,

HAr21 and HAr22 are the same as or different from each other, and each independently a substituted or unsubstituted heterocyclic group,

HAr21 and -L2-HAr22 are not substituted or unsubstituted pyridyl groups at the same time.

In addition, an exemplary embodiment of the present specification is 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 includes a compound represented by Formula 1 do.

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

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

The present specification provides a compound represented by the following formula (1). 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 low driving voltage and excellent lifespan characteristics.

[Formula 1]

In Formula 1,

L2 is a direct bond; A substituted or unsubstituted alkylene group; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Ar21 is a substituted or unsubstituted aryl group,

HAr21 and HAr22 are the same as or different from each other, and each independently a substituted or unsubstituted heterocyclic group,

HAr21 and -L2-HAr22 are not substituted or unsubstituted pyridyl groups at the same time.

는 화학식 또는 화합물에 결합되는 위치를 의미한다.In this specification,

Means a position bonded to a chemical formula or compound.

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. , 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.

In the present specification, the term "substituted or unsubstituted" refers to an alkyl 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.

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 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 the straight chain or 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 an adjacent group 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 the aliphatic hydrocarbon ring 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.

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

In the present specification, 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 heteroarylene group is divalent.

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.

Formula 1 according to the present invention is characterized in that the aryl group is substituted at the 2nd position of the carbazole, and the heterocyclic group is substituted at the 6th and 9th positions. /Or the characteristics of long life.

Specifically, in the compound represented by Formula 1 according to the present invention, the aryl group is substituted at the 2nd position of the carbazole to complement the thermal stability of the compound, and the heterocyclic group is substituted at the 6th and 9th positions, respectively, so that the weak n- There is an effect of adding the type property, so it can act as an n-type host.

Hereinafter, Formula 1 will be described in detail.

[Formula 1]

In Formula 1,

L2 is a direct bond; A substituted or unsubstituted alkylene group; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Ar21 is a substituted or unsubstituted aryl group,

HAr21 and HAr22 are the same as or different from each other, and each independently a substituted or unsubstituted heterocyclic group,

HAr21 and -L2-HAr22 are not substituted or unsubstituted pyridyl groups at the same time.

According to an exemplary embodiment of the present specification, L2 is a direct bond; A substituted or unsubstituted C1 to C60 alkylene group; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C2 to C60 heteroarylene group.

According to an exemplary embodiment of the present specification, L2 is a direct bond; A substituted or unsubstituted C1-C30 alkylene group; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heteroarylene group.

According to an exemplary embodiment of the present specification, L2 is a direct bond; A substituted or unsubstituted C 1 to C 20 alkylene group; A substituted or unsubstituted arylene group having 6 to 20 carbon atoms; Or a substituted or unsubstituted C2 to C20 heteroarylene group.

According to an exemplary embodiment of the present specification, L2 is a direct bond; A substituted or unsubstituted C 1 to C 15 alkylene group; A substituted or unsubstituted arylene group having 6 to 15 carbon atoms; Or a substituted or unsubstituted C 2 to C 15 heteroarylene group.

According to an exemplary embodiment of the present specification, L2 is a direct bond; A substituted or unsubstituted C1-C10 alkylene group; A substituted or unsubstituted arylene group having 6 to 10 carbon atoms; Or a substituted or unsubstituted C2 to C10 heteroarylene group.

According to an exemplary embodiment of the present specification, L2 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.

According to an exemplary embodiment of the present specification, L2 is a direct bond; Or it is an arylene group.

According to an exemplary embodiment of the present specification, L2 is a direct bond; Or an arylene group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L2 is a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; Or a substituted or unsubstituted naphthylene group.

According to an exemplary embodiment of the present specification, L2 is a direct bond; A substituted or unsubstituted phenylene group; Or a substituted or unsubstituted biphenylene group.

According to an exemplary embodiment of the present specification, L2 is a direct bond; Phenylene group; Or a biphenylene group.

According to an exemplary embodiment of the present specification, L2 is a direct bond, or is selected from the following structural formulas.

는 결합위치를 의미한다.In the above structural formula,

Means the bonding position.

According to an exemplary embodiment of the present specification, L2 is a direct bond.

According to an exemplary embodiment of the present specification, Ar21 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

According to an exemplary embodiment of the present specification, Ar21 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar21 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, Ar21 is a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.

According to an exemplary embodiment of the present specification, Ar21 is a substituted or unsubstituted aryl group having 6 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, Ar21 is an aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar21 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; Or a substituted or unsubstituted fluorenyl group.

According to an exemplary embodiment of the present specification, Ar21 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; Or a substituted or unsubstituted fluorenyl group.

According to an exemplary embodiment of the present specification, Ar21 is 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, Ar21 is a phenyl group; Biphenyl group; Or a naphthyl group.

According to an exemplary embodiment of the present specification, Ar21 is a phenyl group; Or a naphthyl group.

According to an exemplary embodiment of the present specification, Ar21 is a phenyl group; 1-naphthyl group; Or 2-naphthyl group.

According to an exemplary embodiment of the present specification, Ar21 is represented by any one of the following structural formulas.

는 결합위치를 의미한다.In the above structural formula,

Means the bonding position.

According to an exemplary embodiment of the present specification, Ar21 is represented by any one of the following structural formulas.

는 결합위치를 의미한다.In the above structural formula,

Means the bonding position.

According to an exemplary embodiment of the present specification, HAr21 and HAr22 are the same as or different from each other, and each independently a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

According to an exemplary embodiment of the present specification, HAr21 and HAr22 are the same as or different from each other, and each independently a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, HAr21 and HAr22 are the same as or different from each other, and each independently a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms.

According to an exemplary embodiment of the present specification, HAr21 and HAr22 are the same as or different from each other, and each independently a substituted or unsubstituted heterocyclic group having 2 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, HAr21 and HAr22 are the same as or different from each other, and each independently a heterocyclic group unsubstituted or substituted with an aryl group.

According to an exemplary embodiment of the present specification, HAr21 and HAr22 are the same as or different from each other, and each independently a heterocyclic group having 2 to 30 carbon atoms including N, O or S unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms to be.

According to an exemplary embodiment of the present specification, HAr21 and HAr22 are the same as or different from each other, and each independently a substituted or unsubstituted pyridyl group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.

According to an exemplary embodiment of the present specification, HAr21 is a substituted or unsubstituted pyridyl group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.

According to an exemplary embodiment of the present specification, HAr21 is a pyridyl group unsubstituted or substituted with an aryl group; A dibenzofuran group unsubstituted or substituted with an aryl group; Or a dibenzothiophene group unsubstituted or substituted with an aryl group.

According to an exemplary embodiment of the present specification, HAr21 is a pyridyl group unsubstituted or substituted with a phenyl group; Dibenzofuran group; Or a dibenzothiophene group.

According to an exemplary embodiment of the present specification, HAr21 is a pyridyl group; Phenylpyridyl group; Diphenylpyridyl group; Dibenzofuran group; Or a dibenzothiophene group.

According to an exemplary embodiment of the present specification, HAr21 is a dibenzofuran group; Or a dibenzothiophene group.

According to an exemplary embodiment of the present specification, HAr21 is a pyridyl group unsubstituted or substituted with a phenyl group.

According to an exemplary embodiment of the present specification, HAr21 is a phenylpyridyl group; Diphenylpyridyl group; Dibenzofuran group; Or a dibenzothiophene group.

According to an exemplary embodiment of the present specification, HAr22 is a substituted or unsubstituted pyridyl group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.

According to an exemplary embodiment of the present specification, HAr22 is a pyridyl group unsubstituted or substituted with an aryl group; A dibenzofuran group unsubstituted or substituted with an aryl group; Or a dibenzothiophene group unsubstituted or substituted with an aryl group.

According to an exemplary embodiment of the present specification, HAr22 is a pyridyl group unsubstituted or substituted with a phenyl group; Dibenzofuran group; Or a dibenzothiophene group.

According to an exemplary embodiment of the present specification, HAr22 is a pyridyl group; Phenylpyridyl group; Diphenylpyridyl group; Dibenzofuran group; Or a dibenzothiophene group.

According to an exemplary embodiment of the present specification, HAr22 is a pyridyl group; Phenylpyridyl group; Dibenzofuran group; Or a dibenzothiophene group.

According to an exemplary embodiment of the present specification, HAr22 is a dibenzofuran group; Or a dibenzothiophene group.

According to an exemplary embodiment of the present specification, HAr22 is a pyridyl group unsubstituted or substituted with a phenyl group.

According to an exemplary embodiment of the present specification, HAr21 and HAr22 are dibenzofuran groups.

According to an exemplary embodiment of the present specification, HAr21 and HAr22 are dibenzothiophene groups.

According to an exemplary embodiment of the present specification, HAr21 is a dibenzofuran group, and HAr22 is a dibenzothiophene group.

According to an exemplary embodiment of the present specification, HAr21 is a dibenzofuran group, and HAr22 is a pyridyl group unsubstituted or substituted with a phenyl group.

According to an exemplary embodiment of the present specification, HAr21 is a dibenzothiophene group, and HAr22 is a dibenzofuran group.

According to an exemplary embodiment of the present specification, HAr21 is a dibenzothiophene group, and HAr22 is a pyridyl group unsubstituted or substituted with a phenyl group.

According to an exemplary embodiment of the present specification, HAr21 is a pyridyl group unsubstituted or substituted with a phenyl group, and HAr22 is a dibenzofuran group.

According to an exemplary embodiment of the present specification, HAr21 is a pyridyl group substituted or unsubstituted with a phenyl group, and HAr22 is a dibenzothiophene group.

According to an exemplary embodiment of the present specification, at least one of HAr21 and HAr22 is a dibenzofuran group; Or a dibenzothiophene group.

According to an exemplary embodiment of the present specification, one of HAr21 and HAr22 is a pyridyl group unsubstituted or substituted with a phenyl group.

According to an exemplary embodiment of the present specification, HAr21 and HAr22 are the same as or different from each other, and each independently selected from the following structural formulas.

는 결합위치를 의미한다.In the above structural formula,

Means the bonding position.

According to an exemplary embodiment of the present specification, HAr21 and HAr22 are the same as or different from each other, and each independently selected from the following structural formulas.

는 결합위치를 의미한다.In the above structural formula,

Means the bonding position.

According to an exemplary embodiment of the present specification, HAr21 and -L2-HAr22 are not a substituted or unsubstituted pyridyl group at the same time.

According to an exemplary embodiment of the present specification, at least one of HAr21 and -L2-HAr22 is a dibenzofuran group; Or a dibenzothiophene group.

In Formula 1 of the present invention, when HAr21 and -L2-HAr22 are not a substituted or unsubstituted pyridyl group at the same time, and at least one of HAr21 and HAr22 contains a dibenzofuran group or a dibenzothiophene group, the compound is somewhat It becomes more robust and has thermal stability. In addition, since HAr21 and -L2-HAr22 are simultaneously substituted or unsubstituted pyridyl groups, LUMO is lowered, and thus n-type characteristics can be more easily controlled.

According to an exemplary embodiment of the present specification, when at least one of HAr21 and -L2-HAr22 is a substituted or unsubstituted pyridyl group, the other is a substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.

According to an exemplary embodiment of the present specification, HAr21 is a pyridyl group unsubstituted or substituted with a phenyl group, and -L2-HAr22 is a dibenzofuran group or a dibenzothiophene group.

According to an exemplary embodiment of the present specification, HAr21 is a diphenylpyridyl group, and -L2-HAr22 is a dibenzofuran group or a dibenzothiophene group.

According to an exemplary embodiment of the present specification, -L2-HAr22 is a pyridyl group unsubstituted or substituted with a phenyl group, and HAr21 is a dibenzofuran group or a dibenzothiophene group.

According to an exemplary embodiment of the present specification, -L2-HAr22 is a diphenylpyridyl group, and HAr21 is a dibenzofuran group or a dibenzothiophene group.

According to an exemplary embodiment of the present specification, HAr21 and HAr22 are not a substituted or unsubstituted pyridyl group at the same time.

According to an exemplary embodiment of the present specification, when at least one of HAr21 and HAr22 is a substituted or unsubstituted pyridyl group, the other is a substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.

According to an exemplary embodiment of the present specification, HAr21 is a pyridyl group unsubstituted or substituted with a phenyl group, and HAr22 is a dibenzofuran group or a dibenzothiophene group.

According to an exemplary embodiment of the present specification, HAr21 is a diphenylpyridyl group, and HAr22 is a dibenzofuran group or a dibenzothiophene group.

According to an exemplary embodiment of the present specification, HAr22 is a pyridyl group substituted or unsubstituted with a phenyl group, and HAr21 is a dibenzofuran group or a dibenzothiophene group.

According to an exemplary embodiment of the present specification, HAr22 is a diphenylpyridyl group, and HAr21 is a dibenzofuran group or a dibenzothiophene group.

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

[Formula 1-1]

In Formula 1-1, the definitions of Ar21 and L2 are the same as those in Formula 1,

X21 and X22 are the same as or different from each other, and each independently O; Or S,

R21 and R22 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

r21 and r22 are each an integer of 0 to 7, when r21 is 2 or more, two or more R21s are the same as or different from each other, and when r22 is 2 or more, two or more R22s are the same or different from each other.

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

[Formula 2-1]

[Formula 2-2]

In Formulas 2-1 and 2-2, the definitions of Ar21 and L2 are the same as those in Formula 1,

X21 and X22 are the same as or different from each other, and each independently O; Or S,

R21 to R23 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

r21 and r22 are each an integer of 0 to 7, when r21 is 2 or more, two or more R21s are the same as or different from each other, and when r22 is 2 or more, two or more R22s are the same or different from each other,

r23 is an integer of 0 to 4, and when r23 is 2 or more, 2 or more R23s are the same as or different from each other.

According to an exemplary embodiment of the present specification, X21 and X22 are O.

According to an exemplary embodiment of the present specification, X21 and X22 are S.

According to an exemplary embodiment of the present specification, X21 is O, and X22 is S.

According to an exemplary embodiment of the present specification, X21 is S, and X22 is O.

According to an exemplary embodiment of the present specification, R21 to R23 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

According to an exemplary embodiment of the present specification, R21 to R23 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heterocyclic group.

According to an exemplary embodiment of the present specification, R21 to R23 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted C2 to C20 heterocyclic group.

According to an exemplary embodiment of the present specification, R21 and R22 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted aryl group.

According to an exemplary embodiment of the present specification, R21 and R22 are the same as or different from each other, and each independently hydrogen; Or deuterium.

According to an exemplary embodiment of the present specification, R21 and R22 are hydrogen.

[0366] According to an exemplary embodiment of the present specification, R23 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted aryl group.

[0366] According to an exemplary embodiment of the present specification, R23 is hydrogen; Or a substituted or unsubstituted aryl group.

[0366] According to an exemplary embodiment of the present specification, R23 is hydrogen; Or an aryl group.

[0366] According to an exemplary embodiment of the present specification, R23 is hydrogen; Or, it is a C6-C30 aryl group.

[0366] According to an exemplary embodiment of the present specification, R23 is hydrogen; Or a phenyl group.

According to an exemplary embodiment of the present specification, r21 and r22 are integers of 0 to 2, respectively.

According to an exemplary embodiment of the present specification, r21 and r22 are 0 or 1, respectively.

According to an exemplary embodiment of the present specification, r23 is an integer of 0 to 3.

According to an exemplary embodiment of the present specification, r23 is an integer of 0 to 2.

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

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

<Reaction Scheme 1>

In Reaction Scheme 1, the definition of the substituent is the same as the definition in Formula 1.

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.

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

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 case, the compound refers to a compound represented by Formula 1.

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 light-emitting device of the present specification may be manufactured by a conventional method and material for manufacturing an organic light-emitting device, except for forming one or more organic material layers using the compound.

When manufacturing an organic light-emitting device in which an organic material layer including the compound is formed may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.

The organic material layer of the organic light emitting device of the present specification may have a single-layer structure, but may have a 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 is an emission layer, and the emission layer includes the compound.

In the exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes the compound.

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

In the exemplary embodiment of the present specification, the organic material layer includes a phosphorescent emission layer, and the phosphorescent emission layer includes the compound as a host of the emission layer.

In the exemplary embodiment of the present specification, the organic material layer includes a delayed fluorescence emission layer, and the delayed fluorescence emission layer includes the compound as a host of the emission layer.

In the exemplary embodiment of the present specification, the thickness of the organic material layer including the compound of Formula 1 is 5 Å to 500 Å, preferably 10 Å to 400 Å, and more preferably 50 Å to 300 Å.

In another exemplary embodiment, the thickness of the organic material layer including the compound of Formula 1 is 10 nm to 500 nm, preferably 50 nm to 400 nm, and more preferably 100 nm to 350 nm.

In the exemplary embodiment of the present specification, the compound may be used as a hole-transporting host, an electron-transporting host, or a bipolar host depending on the substituent.

In the exemplary embodiment of the present specification, the emission layer may further include a host material other than the compound, and the host may include a condensed aromatic ring derivative or a heterocyclic-containing compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, 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 emission layer may include the compound, and may further include a phosphorescent material or a delayed fluorescent compound. The delayed fluorescent compound is a light-emitting organic compound in which a gap (ΔEst) between the lowest triplet state T1 and the first excited singlet state S1 is 0.2 eV or less.

When the gap (ΔEst) between the first excited singlet state S1 and the lowest triplet state T1 of the delayed fluorescent compound satisfies the above range, the excitons generated in the triplet are moved to the singlet by the inverse interphase transition (RISC). The increase in the rate and speed increases the time that exciton stays in the triplet, so there is an advantage of increasing the efficiency and life of the organic light-emitting device.

In the exemplary embodiment of the present specification, when a delayed fluorescent compound is further included in the emission layer, the delayed fluorescent compound 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 compound, and preferably 1 part by weight It may be included in to 30 parts by weight, more preferably 5 to 20 parts by weight.

According to the exemplary embodiment of the present specification, the delayed fluorescent compound may act as a dopant in the emission layer.

According to an exemplary embodiment of the present specification, the delayed fluorescent compound may be selected from one or more of the following structural formulas.

In the exemplary embodiment of the present specification, the emission layer may include the compound and may further include a dopant. In this case, the dopant may be a phosphorescent dopant, and the dopant may be included in an amount of 0.1 to 50 parts by weight based on 100 parts by weight of the host, preferably 1 to 30 parts by weight, more preferably 5 to 20 parts by weight. It may be included in parts by weight of.

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

In the organic light emitting device of the present specification, the organic material layer may include an electron blocking layer, and the electron blocking layer may include a compound represented by Formula 1 described above.

In the organic light emitting device of the present specification, the organic material layer includes an electron transport layer, an electron injection layer, or an electron transport and injection layer, and the electron transport layer, the electron injection layer, or the electron transport and injection layer is represented by Formula 1 above. It may contain a compound.

In the organic light emitting device of the present specification, the organic material layer may include an electron controlling layer, and the electron controlling layer may include a compound represented by Formula 1 described above.

In the organic light emitting device of the present specification, the organic material layer includes a hole blocking layer, and the hole blocking layer includes the compound represented by Formula 1 above.

In the exemplary embodiment of the present specification, the organic light emitting device 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 one 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 the compound.

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 first electrode is an anode, and the second electrode is a cathode.

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

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

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

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

(3) Anode/Hole Transport Layer/Light-Emitting Layer/Electron Transport Layer/Anode

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

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

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

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

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

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

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

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

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

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

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

For example, the structure of an organic light-emitting device according to an exemplary embodiment of the present specification is illustrated in FIGS. 1 to 3. 1 to 3 illustrate an organic light emitting device, but 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 5, and a cathode 9 are sequentially stacked. In such a structure, the compound may be included in the light emitting layer 5.

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

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

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 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 PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, and uses a metal or conductive metal oxide or alloy thereof on a substrate. Deposited to form an anode, formed by 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. 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 be a multi-layered structure including a hole injection layer, a hole transport layer, a layer that simultaneously injects and transports electrons, an electron blocking layer, a light emitting layer and an electron transport layer, an electron injection layer, a layer that simultaneously injects and transports electrons, etc. However, the present invention is not limited thereto and may have a single layer structure. In addition, the organic material layer is made of a variety of polymer materials, and is used in a smaller number of solvent processes, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. It can be made in layers.

The positive electrode is an electrode for injecting holes, and a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer as the positive electrode material. 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); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.

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 that electrons can be easily injected into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; There are multilayered materials such as LiF/Al or LiO ₂ /Al, but are not limited thereto.

The hole injection layer is a layer that facilitates injection of holes from the anode to the light emitting layer, and the hole injection material is a material capable of well injecting holes from the anode at a low voltage. It is preferable that molecular orbital) is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. Organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited thereto. The thickness of the hole injection layer may be 1 to 150 nm. When the thickness of the hole injection layer is 1 nm or more, there is an advantage of preventing deterioration of the hole injection characteristics, and when the thickness of the hole injection layer is 150 nm or less, the thickness of the hole injection layer is too thick to increase the driving voltage to improve the movement of holes. There is an advantage that can be prevented.

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

An electron blocking layer may be provided between the hole transport layer and the light emitting layer. Materials known in the art may be used for the electron blocking layer.

The emission layer may emit red, green, or blue light, and may be made of a phosphorescent material or a fluorescent material. As the light-emitting material, a material capable of emitting light in a visible light region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency 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 compound; Benzoxazole, benzthiazole, and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

Examples of the host material for the light emitting layer include a condensed aromatic ring derivative or a heterocyclic compound. Specifically, except for the compound represented by Formula 1 of the present invention, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and heterocycle-containing compounds Examples include, but are not limited to, carbazole derivatives, dibenzofuran derivatives, ladder furan compounds, and pyrimidine derivatives.

When the emission layer emits red light, the emission dopants include PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium). ), a phosphorescent material such as octaethylporphyrin platinum (PtOEP), or a _{fluorescent material such as Alq 3} (tris(8-hydroxyquinolino)aluminum), but is not limited thereto. When the emission layer emits green light, the emission dopant is a _{phosphorescent material such as Ir(ppy) 3} (fac tris(2-phenylpyridine)iridium), Alq3(tris(8-hydroxyquinolino)aluminum), anthracene compound, pyrene type A fluorescent material such as a compound or a boron-based compound may be used, but 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, distillbenzene (DSB), distrylarylene (DSA), A fluorescent material such as a PFO-based polymer, a PPV-based polymer, an anthracene-based compound, a pyrene-based compound, or a boron-based compound may be used, but is not limited thereto.

The electron transport layer may play a role of facilitating transport of electrons. As the electron transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable, and a material having high mobility for electrons is suitable. Specific examples include Al complex of 8-hydroxyquinoline; Complexes containing Alq _3; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The thickness of the electron transport layer may be 1 to 50 nm. If the thickness of the electron transport layer is 1 nm or more, there is an advantage of preventing deterioration of the electron transport characteristics, and if the thickness of the electron transport layer is 50 nm or less, the thickness of the electron transport layer is too thick to prevent an increase in the driving voltage to improve the movement of electrons. There is an advantage to be able to.

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

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

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, BCP, aluminum complexes, etc., 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.

<Synthesis Example>

Synthesis Example 1: Synthesis of Compound 1.

Synthesis of Intermediate 1-1

The 2-bromo-6-chloro-9H-carbazole 10.0g (35.64mmol), phenylboronic acid 4.35g (35.64mmol) and tetrakis (triphenylphosphine) palladium 2mol% were added to 100ml of tetrahydrofuran and potassium carbonate (potassium carbonate) 14.78g (106.92mmol) was dissolved in 50ml of water and mixed. After stirring at 80° C. for 12 hours, the reaction was terminated and cooled to room temperature to separate water and an organic layer. Only the organic layer was taken, anhydrous magnesium sulfate was added thereto, stirred, filtered through a silica pad, and the solution was concentrated under reduced pressure. Then, the column was purified to obtain 8.12g (82% yield) of Intermediate 1-1.

Synthesis of Intermediate 1-2

Intermediate 1-1 8.12g(29.23mmol), 4-bromodibenzo[b,d]furan 7.22g(29.23mmol), bis(tri-ter-butylphosphine)palladium(0) 1mol% and NaOt-Bu 3.37g ( 35.08mmol) was added to 90ml toluene and stirred at 110°C for 12 hours. After completion of the reaction, the mixture was cooled to room temperature and filtered through a silica pad to remove impurities. After filtration, the solution was washed with water, only the organic layer was taken, anhydrous magnesium sulfate was added thereto, stirred, filtered through a silica pad, and the solution was concentrated under reduced pressure. Then, column purification was performed to obtain 8.30 g (64% yield) of Intermediate 1-2.

Synthesis of compound 1

Intermediate 1-2 8.30g(18.70mmol), dibenzo[b,d]furan-4-ylboronic acid 3.96g(18.70mmol), bis(tri-ter-butylphosphine)palladium(0) 1mol% and NaOt-Bu 2.16g (22.44mmol) was added to 55ml toluene and stirred at 110°C for 12 hours. After completion of the reaction, the mixture was cooled to room temperature and filtered through a silica pad to remove impurities. After filtration, the solution was washed with water, only the organic layer was taken, anhydrous magnesium sulfate was added thereto, stirred, filtered through a silica pad, and the solution was concentrated under reduced pressure. Then, column purification was performed to obtain 8.83 g (82% yield) of compound 1

MS: [M+H]+= 576

Synthesis Example 2: Synthesis of Compound 2.

Synthesis of Intermediate 2-1

Intermediate 1-1 8.12g(29.23mmol), 1-bromodibenzo[b,d]furan 7.22g(29.23mmol), bis(tri-ter-butylphosphine)palladium(0) 1mol% and NaOt-Bu 3.37g ( 35.08mmol) was added to 90ml toluene and stirred at 110°C for 12 hours. After completion of the reaction, the mixture was cooled to room temperature and filtered through a silica pad to remove impurities. After filtration, the solution was washed with water, only the organic layer was taken, anhydrous magnesium sulfate was added thereto, stirred, filtered through a silica pad, and the solution was concentrated under reduced pressure. Then, column purification was performed to obtain 8.69 g (67% yield) of Intermediate 2-1.

Synthesis of compound 2

Intermediate 1-2 8.69g(19.58mmol), dibenzo[b,d]thiophen-4-ylboronic acid 4.46g(19.58mmol), bis(tri-ter-butylphosphine)palladium(0) 1mol% and NaOt-Bu 2.26g (23.50mmol) was added to 60ml toluene and stirred at 110°C for 12 hours. After completion of the reaction, the mixture was cooled to room temperature and filtered through a silica pad to remove impurities. After filtration, the solution was washed with water, only the organic layer was taken, anhydrous magnesium sulfate was added thereto, stirred, filtered through a silica pad, and the solution was concentrated under reduced pressure. Then, the column was purified to obtain 9.15 g (79% yield) of compound 2.

MS: [M+H]+= 592

Synthesis Example 3: Synthesis of Compound 3.

Synthesis of Intermediate 3-1

Intermediate 1-1 8.12g (29.23mmol), 3-bromodibenzo[b,d]thiophene 7.69g (29.23mmol) was reacted and purified in the same manner as in the synthesis of Intermediate 2-1, to obtain Intermediate 3-1. 8.47g (63% yield) was obtained.

Synthesis of compound 3

Intermediate 3-1 8.47g (18.41mmol), dibenzo[b,d]furan-2-ylboronic acid 3.90g (18.41mmol) was reacted and purified in the same manner as the synthesis of compound 2, except that compound 3 was 8.06 g (74% yield) was obtained.

MS: [M+H]+= 592

Synthesis Example 4: Synthesis of compound 4.

Synthesis of Intermediate 4-1

Intermediate 1-1 8.12g (29.23mmol), 2-bromodibenzo[b,d]thiophene 7.69g (29.23mmol) was reacted and purified in the same manner as in the synthesis of Intermediate 2-1, to obtain Intermediate 4-1. 8.88g (66% yield) was obtained.

Synthesis of compound 4

Intermediate 4-1 8.88g (19.30mmol), dibenzo[b,d]thiophen-4-ylboronic acid 4.40g (19.30mmol) was reacted and purified in the same manner as in the synthesis of compound 2, to obtain compound 4 in 8.21. g (70% yield) was obtained.

MS: [M+H]+= 608

Synthesis Example 5: Synthesis of compound 5.

Synthesis of Intermediate 5-1

Intermediate 1-1 8.12g (29.23mmol), 4-bromodibenzo[b,d]furan 7.22g (29.23mmol) was reacted and purified in the same manner as in the synthesis of Intermediate 2-1, to obtain Intermediate 5-1. 8.44 g (65% yield) were obtained.

Synthesis of compound 5

Intermediate 5-1 8.44g (19.01mmol), (3,5-diphenylpyridin-2-yl)boronic acid 5.23g (19.01mmol) was reacted and purified in the same manner as in the synthesis of compound 2, except for using compound 5 7.41 g (61% yield) was obtained.

MS: [M+H]+= 639

Synthesis Example 6: Synthesis of Compound 6.

Synthesis of Intermediate 6-1

Intermediate 1-1 8.12g (29.23mmol), 2-bromodibenzo[b,d]thiophene 7.69g (29.23mmol) was reacted and purified in the same manner as in the synthesis of Intermediate 2-1, to obtain Intermediate 6-1. 9.15 g (68% yield) were obtained.

Synthesis of compound 6

Intermediate 6-1 9.15g (19.89mmol), (5-phenylpyridin-3-yl)boronic acid 3.96g (19.89mmol) was reacted and purified in the same manner as in the synthesis of compound 2 except for using 7.25g of compound 6 (Yield 63%) was obtained.

MS: [M+H]+= 579

Synthesis Example 7: Synthesis of compound 7.

Synthesis of Intermediate 7-1

Intermediate 1-1 8.12g (29.23mmol), 2-bromopyridine 4.62g (29.23mmol) was reacted and purified in the same manner as the synthesis of Intermediate 2-1 except for using 6.53g (yield 63%) ) Was obtained.

Synthesis of compound 7

Intermediate 7-1 6.53g (13.42mmol), dibenzo[b,d]furan-4-ylboronic acid 2.85g (13.42mmol) was reacted and purified in the same manner as the synthesis of compound 2, except that compound 7 was 4.31 g (66% yield) was obtained.

MS: [M+H]+= 487

Synthesis Example 8: Synthesis of compound 8.

Synthesis of Intermediate 8-1

Intermediate 1-1 8.12g (29.23mmol), 4-bromo-3-phenylpyridine 6.84g (29.23mmol) was reacted and purified in the same manner as the synthesis of Intermediate 2-1 except for using 7.05g of Intermediate 8-1 (Yield 56%) was obtained.

Synthesis of compound 8

Intermediate 8-1 7.05g (16.36mmol), dibenzo[b,d]thiophen-3-ylboronic acid 3.73g (16.36mmol) was reacted and purified in the same manner as the synthesis of compound 2, except that compound 8 was 6.34 g (yield 67%) was obtained.

MS: [M+H]+= 579

Synthesis Example 9: Synthesis of compound 9.

Synthesis of Intermediate 9-1

Except for using 2-bromo-6-chloro-9H-carbazole 10.0g (35.64mmol) and naphthalen-1-ylboronic acid 6.13g (35.64mmol), reacted and purified in the same manner as in the synthesis of Intermediate 1-1. 7.83g (yield 67%) of Intermediate 9-1 was obtained.

Synthesis of Intermediate 9-2

Intermediate 9-1 7.83g (23.89mmol), 4-bromodibenzo[b,d]furan 5.90g (23.89mmol) was reacted and purified in the same manner as in the synthesis of Intermediate 1-2, to obtain Intermediate 9-2. 7.20g (61% yield) was obtained.

Synthesis of compound 9

Intermediate 9-2 7.20g (14.58mmol), dibenzo[b,d]furan-4-ylboronic acid 3.09g (14.58mmol) was reacted and purified in the same manner as the synthesis of compound 1, except that compound 9 was 5.75 g (63% yield) was obtained.

MS: [M+H]+= 626

Synthesis Example 10: Synthesis of compound 10.

Synthesis of Intermediate 10-1

Intermediate 9-1 7.83g (23.89mmol), 4-bromodibenzo[b,d]thiophene 6.29g (23.89mmol) was reacted and purified in the same manner as in the synthesis of Intermediate 9-2, to obtain Intermediate 10-1. 7.80g (64% yield) was obtained.

Synthesis of compound 10

Intermediate 10-1 7.80g (15.29mmol), (6-phenylpyridin-3-yl)boronic acid 3.04g (15.29mmol) was reacted in the same manner as in the synthesis of compound 1, except for using 5.67g of compound 10 by purification (Yield 59%) was obtained.

MS: [M+H]+= 626

Synthesis Example 11: Synthesis of compound 11.

Synthesis of Intermediate 11-1

Except for using 2-bromo-6-chloro-9H-carbazole 10.0g (35.64mmol) and naphthalen-2-ylboronic acid 6.13g (35.64mmol), reacted and purified in the same manner as in the synthesis of Intermediate 1-1. 8.18g (70% yield) of Intermediate 11-1 was obtained.

Synthesis of Intermediate 11-2

Intermediate 11-1 8.18g (24.95mmol), 2-bromodibenzo[b,d]thiophene 6.57g (24.95mmol) was reacted and purified in the same manner as in the synthesis of Intermediate 1-2 above to obtain Intermediate 11-2. 8.40g (66% yield) was obtained.

Synthesis of compound 11

Intermediate 11-2 8.40g (16.47mmol), dibenzo[b,d]thiophen-4-ylboronic acid 3.76g (16.47mmol) was reacted and purified in the same manner as the synthesis of compound 1, except that compound 11 was 6.50 g (yield 60%) was obtained.

MS: [M+H]+= 658

Synthesis Example 12: Synthesis of compound 12.

Synthesis of Intermediate 12-1

Intermediate 11-1 8.18g (24.95mmol), 2-bromo-6-phenylpyridine 5.84g (24.95mmol) was reacted and purified in the same manner as the synthesis of Intermediate 1-2, except for using 6.96g of Intermediate 12-1 (Yield 58%) was obtained.

Synthesis of compound 12

Intermediate 12-1 6.96g (14.47mmol), dibenzo[b,d]thiophen-2-ylboronic acid 3.30g (14.47mmol) was reacted and purified in the same manner as in the synthesis of compound 1, and compound 12 was 5.82 g (64% yield) was obtained.

MS: [M+H]+= 629

<Example 1>

Example 1-1: Fabrication of an organic light-emitting device to which compound 1 is applied

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. In this case, Fischer Co. product was used as a detergent, and distilled water secondarily filtered with a filter made 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.

DNTPD was thermally vacuum deposited to a thickness of 600Å on the prepared ITO transparent electrode to form a hole injection layer. 50Å of BPBPA and 600Å of PCZAC were sequentially vacuum-deposited on the hole injection layer to form a hole transport layer. Subsequently, compound 1 and 4CzIPN according to Synthesis Example 1 were vacuum-deposited on the hole transport layer at a weight ratio of 20:1 with a film thickness of 200Å to form a light emitting layer.

DBFTrz (50Å) and ZADN (300Å) were sequentially deposited on the emission layer to form an electron transport layer. Lithium fluoride (LiF) at a thickness of 10 Å and aluminum at a thickness of 1,000 Å were sequentially deposited on the electron transport layer to form an electron injection layer and a negative electrode.

In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.9 Å/sec, the deposition rate of lithium fluoride at the cathode was 0.3 Å/sec, and the deposition rate of aluminum was 2 Å/sec, and the vacuum degree during deposition was 1 Х 10 ^{Maintaining -7} to 5 Х 10 ^-8 torr, an organic light emitting device was manufactured.

Example 1-2: Fabrication of an organic light-emitting device to which compound 2 is applied

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that Compound 2 according to Synthesis Example 2 was used instead of Compound 1 in Example 1-1.

Example 1-3: Fabrication of an organic light-emitting device to which compound 3 is applied

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that Compound 3 according to Synthesis Example 3 was used instead of Compound 1 in Example 1-1.

Example 1-4: Fabrication of an organic light-emitting device to which compound 4 is applied

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that Compound 4 according to Synthesis Example 4 was used instead of Compound 1 in Example 1-1.

Example 1-5: Fabrication of an organic light-emitting device to which compound 5 is applied

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that Compound 5 according to Synthesis Example 5 was used instead of Compound 1 in Example 1-1.

Example 1-6: Fabrication of an organic light-emitting device to which compound 6 is applied

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that Compound 6 according to Synthesis Example 6 was used instead of Compound 1 in Example 1-1.

Example 1-7: Fabrication of an organic light-emitting device to which compound 7 is applied

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that Compound 7 according to Synthesis Example 7 was used instead of Compound 1 in Example 1-1.

Example 1-8: Fabrication of an organic light-emitting device to which compound 8 is applied

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that Compound 8 according to Synthesis Example 8 was used instead of Compound 1 in Example 1-1.

Example 1-9: Fabrication of an organic light-emitting device to which compound 9 is applied

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that Compound 9 according to Synthesis Example 9 was used instead of Compound 1 in Example 1-1.

Example 1-10: Fabrication of an organic light-emitting device to which compound 10 is applied

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that Compound 10 according to Synthesis Example 10 was used instead of Compound 1 in Example 1-1.

Example 1-11: Fabrication of an organic light-emitting device to which compound 11 is applied

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that Compound 11 according to Synthesis Example 11 was used instead of Compound 1 in Example 1-1.

Example 1-12: Fabrication of an organic light-emitting device to which compound 12 is applied

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that Compound 12 according to Synthesis Example 12 was used instead of Compound 1 in Example 1-1.

<Comparative Example 1>

Comparative Example 1-1: Fabrication of an organic light-emitting device to which the comparative compound GH 1 is applied

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the following Comparative Example compound GH 1 was used instead of Compound 1.

Comparative Example 1-2: Fabrication of an organic light-emitting device to which the comparative compound GH 2 was applied

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the following Comparative Example Compound GH 2 was used instead of Compound 1.

Comparative Example 1-3: Fabrication of an organic light-emitting device to which the comparative compound GH 3 was applied

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the following Comparative Example Compound GH 3 was used instead of Compound 1.

The organic light emitting devices fabricated in Examples 1-1 to 1-12 and Comparative Examples 1-1 to 1-3 were used by Photo Research's PR-655 IVL measuring instrument to measure current-voltage-luminance (current-voltage-luminance: IVL), color coordinate (CIE), and luminous efficiency (LE) characteristics were measured, and the results are shown in Table 1 below.

compound
(Host) Voltage(V)
(@10mA/cm ² ) Efficiency (cd/A)
(@10mA/cm ² ) Color coordinates (x, y)
(CIE) Example 1-1 Compound 1 4.8 33.7 0.34, 0.61 Example 1-2 Compound 2 4.7 36.1 0.33, 0.65 Example 1-3 Compound 3 4.3 33.5 0.31, 0.60 Example 1-4 Compound 4 4.5 35.9 0.35, 0.61 Example 1-5 Compound 5 4.8 34.8 0.33, 0.62 Example 1-6 Compound 6 4.7 33.3 0.33, 0.60 Example 1-7 Compound 7 4.5 36.4 0.34, 0.64 Example 1-8 Compound 8 4.9 34.5 0.34, 0.65 Example 1-9 Compound 9 4.7 33.7 0.32, 0.65 Example 1-10 Compound 10 4.4 36.3 0.35, 0.63 Example 1-11 Compound 11 4.5 35.9 0.34, 0.58 Example 1-12 Compound 12 4.5 34.5 0.33, 0.59 Comparative Example 1-1 GH 1 5.1 28.7 0.33, 0.57 Comparative Example 1-2 GH 2 5.4 27.1 0.32, 0.58 Comparative Example 1-3 GH 3 5.3 25.1 0.33, 0.57

As can be seen from the results of Table 1, Examples 1-1 to 1-12 using the compound of Formula 1 of the present invention have superior voltage and efficiency compared to the case of using the comparative compounds GH 1 to GH 3.

Specifically, the glass transition temperature of the compound of Formula 1 in which an aryl group is substituted is higher than that of Comparative Example compound GH 1 in which the aryl group is not substituted at the position 2 of the carbazole, so that thermal stability is obtained.

In addition, since the LUMO of the compound of Formula 1 containing dibenzofuran or dibenzothiophene is lower than that of the comparative compound GH 2 containing two pyridyl groups, the effect of facilitating energy level control according to the linking position of the substituents. Show.

In addition, since the n-type characteristic of the compound of Formula 1 to which a heteroaryl group is connected is more dominant than Comparative Example compound GH 3 in which only an aryl group is connected at position 9 of the carbazole, it is easier to transfer electrons in the light emitting layer. Shows the effect.

Accordingly, it can be seen that the light emitting device using the compound represented by Formula 1 as a host of the delayed fluorescent light emitting layer has improved luminous efficiency while lowering the driving voltage compared to the light emitting device to which the comparative compounds GH 1 to GH 3 are applied.

<Example 2>

Example 2-1: Fabrication of an organic light-emitting device to which compound 1 is applied

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. In this case, Fischer Co. product was used as a detergent, and distilled water secondarily filtered with a filter made 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 prepared ITO transparent electrode, m-MTDATA(60nm) / TCTA(80 nm) / host + Ir(ppy) ₃ (10 parts by weight compared to 100 parts by weight of host) (300nm) / BCP(10 nm)/ Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm), the light emitting device was configured in the order, and an organic light emitting device was manufactured using Compound 1 according to Synthesis Example 1 as the host.

The structures of m-MTDATA, TCTA, Ir(ppy) ₃ and BCP are as follows, respectively.

Example 2-2: Fabrication of an organic light-emitting device to which compound 2 is applied

An organic light-emitting device was manufactured in the same manner as in Example 2-1, except that Compound 2 according to Synthesis Example 2 was used instead of Compound 1 in Example 2-1.

Example 2-3: Fabrication of an organic light-emitting device to which compound 3 is applied

An organic light-emitting device was manufactured in the same manner as in Example 2-1, except that Compound 3 according to Synthesis Example 3 was used instead of Compound 1 in Example 2-1.

Example 2-4: Fabrication of an organic light-emitting device applying compound 4

An organic light-emitting device was manufactured in the same manner as in Example 2-1, except that Compound 4 according to Synthesis Example 4 was used instead of Compound 1 in Example 2-1.

Example 2-5: Fabrication of an organic light emitting device to which compound 5 is applied

An organic light-emitting device was manufactured in the same manner as in Example 2-1, except that Compound 5 according to Synthesis Example 5 was used instead of Compound 1 in Example 2-1.

Example 2-6: Fabrication of an organic light-emitting device to which compound 6 is applied

An organic light-emitting device was manufactured in the same manner as in Example 2-1, except that Compound 6 according to Synthesis Example 6 was used instead of Compound 1 in Example 2-1.

Example 2-7: Fabrication of an organic light-emitting device to which compound 7 is applied

An organic light-emitting device was manufactured in the same manner as in Example 2-1, except that Compound 7 according to Synthesis Example 7 was used instead of Compound 1 in Example 2-1.

Example 2-8: Fabrication of an organic light-emitting device applying compound 8

An organic light-emitting device was manufactured in the same manner as in Example 2-1, except that Compound 8 according to Synthesis Example 8 was used instead of Compound 1 in Example 2-1.

Example 2-9: Fabrication of an organic light-emitting device to which compound 9 is applied

An organic light-emitting device was manufactured in the same manner as in Example 2-1, except that Compound 9 according to Synthesis Example 9 was used instead of Compound 1 in Example 2-1.

Example 2-10: Fabrication of an organic light-emitting device to which compound 10 is applied

An organic light-emitting device was manufactured in the same manner as in Example 2-1, except that Compound 10 according to Synthesis Example 10 was used instead of Compound 1 in Example 2-1.

Example 2-11: Fabrication of an organic light-emitting device to which compound 11 is applied

An organic light-emitting device was manufactured in the same manner as in Example 2-1, except that Compound 11 according to Synthesis Example 11 was used instead of Compound 1 in Example 2-1.

Example 2-12: Fabrication of an organic light-emitting device to which compound 12 is applied

An organic light-emitting device was manufactured in the same manner as in Example 2-1, except that Compound 12 according to Synthesis Example 12 was used instead of Compound 1 in Example 2-1.

<Comparative Example 2>

Comparative Example 2-1: Fabrication of an organic light-emitting device to which the comparative compound GH 1 is applied

An organic light-emitting device was manufactured in the same manner as in Example 2-1, except that the following Comparative Example Compound GH 1 was used instead of Compound 1.

Comparative Example 2-2: Fabrication of an organic light-emitting device to which the comparative compound GH 2 was applied

An organic light-emitting device was manufactured in the same manner as in Example 2-1, except that the following Comparative Example Compound GH 2 was used instead of Compound 1.

Comparative Example 2-3: Fabrication of an organic light-emitting device to which the comparative compound GH 3 was applied

An organic light-emitting device was manufactured in the same manner as in Example 2-1, except that the following Comparative Example Compound GH 3 was used instead of Compound 1.

The organic light-emitting devices fabricated in Examples 2-1 to 2-12 and Comparative Examples 2-1 to 2-3 were used with a PR-655 IVL meter manufactured by Photo Research Co., Ltd., and current-voltage-luminance (current-voltage-luminance: IVL), color coordinate (CIE), and luminous efficiency (LE) characteristics were measured, and the results are shown in Table 2 below.

compound
(Host) Voltage(V)
(V@19000nit) Efficiency (cd/A)
(cd/A@10000nit) Color coordinates (x, y)
(CIE) Example 2-1 Compound 1 3.65 125.75 (0.249, 0.702) Example 2-2 Compound 2 3.62 127.78 (0.248, 0.706) Example 2-3 Compound 3 3.60 125.96 (0.248, 0.707) Example 2-4 Compound 4 3.61 127.94 (0.247, 0.705) Example 2-5 Compound 5 3.65 126.75 (0.249, 0.702) Example 2-6 Compound 6 3.62 125.78 (0.248, 0.706) Example 2-7 Compound 7 3.60 127.96 (0.248, 0.707) Example 2-8 Compound 8 3.61 126.94 (0.247, 0.705) Example 2-9 Compound 9 3.65 125.75 (0.249, 0.702) Example 2-10 Compound 10 3.62 127.78 (0.248, 0.706) Example 2-11 Compound 11 3.60 127.96 (0.248, 0.707) Example 2-12 Compound 12 3.61 126.94 (0.247, 0.705) Comparative Example 2-1 GH 1 4.11 120.7 (0.247, 0.705) Comparative Example 2-2 GH 2 4.04 121.1 (0.248, 0.702) Comparative Example 2-3 GH 3 4.08 120.9 (0.247, 0.705)

As can be seen from the results of Table 2, Examples 2-1 to 2-12 using the compound of Formula 1 of the present invention have superior voltage and efficiency compared to the case of using the comparative compounds GH 1 to GH 3.

Specifically, the glass transition temperature of the compound of Formula 1 in which an aryl group is substituted is higher than that of Comparative Example compound GH 1 in which the aryl group is not substituted at the position 2 of the carbazole, so that thermal stability is obtained.

In addition, since the LUMO of the compound of Formula 1 containing dibenzofuran or dibenzothiophene is lower than that of the comparative compound GH 2 containing two pyridyl groups, the effect of facilitating energy level control according to the linking position of the substituents. Show.

In addition, since the n-type characteristic of the compound of Formula 1 to which a heteroaryl group is connected is more dominant than Comparative Example compound GH 3 in which only an aryl group is connected at position 9 of the carbazole, it is easier to transfer electrons in the light emitting layer. Shows the effect.

Accordingly, it can be seen that the light emitting device using the compound represented by Formula 1 as a host of the phosphorescent light emitting layer has improved luminous efficiency while lowering the driving voltage compared to the light emitting device to which the comparative compounds GH 1 to GH 3 are applied.

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

Claims (14)

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

In Formula 1,
L2 is a direct bond; A substituted or unsubstituted alkylene group; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar21 is a substituted or unsubstituted aryl group,
HAr21 and HAr22 are the same as or different from each other, and each independently a substituted or unsubstituted heterocyclic group,
HAr21 and -L2-HAr22 are not substituted or unsubstituted pyridyl groups at the same time. The compound of claim 1, wherein L2 is a direct bond. The method according to claim 1, wherein HAr21 and HAr22 are the same as or different from each other, and each independently a substituted or unsubstituted pyridyl group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group. The method according to claim 1,
L2 is a direct bond; Or an arylene group having 6 to 30 carbon atoms,
Ar21 is an aryl group having 6 to 30 carbon atoms,
The HAr21 and HAr22 are the same as or different from each other, and each independently a compound having 2 to 30 carbon atoms including N, O or S unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms. The compound of claim 1, wherein one of HAr21 and HAr22 is a pyridyl group unsubstituted or substituted with a phenyl group. The method according to claim 1, wherein at least one of HAr21 and HAr22 is a dibenzofuran group; Or a compound that is a dibenzothiophene group. The compound of claim 1, wherein the formula 1 is represented by the following formula 1-1:
[Formula 1-1]

In Formula 1-1, the definitions of Ar21 and L2 are the same as those in Formula 1,
X21 and X22 are the same as or different from each other, and each independently O; Or S,
R21 and R22 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
r21 and r22 are each an integer of 0 to 7, when r21 is 2 or more, two or more R21s are the same as or different from each other, and when r22 is 2 or more, two or more R22s are the same or different from each other. The compound of claim 1, wherein the formula 1 is represented by the following formula 2-1 or 2-2:
[Formula 2-1]

[Formula 2-2]

In Formulas 2-1 and 2-2, the definitions of Ar21 and L2 are the same as those in Formula 1,
X21 and X22 are the same as or different from each other, and each independently O; Or S,
R21 to R23 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
r21 and r22 are each an integer of 0 to 7, when r21 is 2 or more, two or more R21s are the same as or different from each other, and when r22 is 2 or more, two or more R22s are the same or different from each other,
r23 is an integer of 0 to 4, and when r23 is 2 or more, 2 or more R23s are the same as or different from each other. The method according to claim 1,
Formula 1 is a compound represented by any one of the following compounds:

. 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 9 Light-emitting element. The method of claim 10,
The organic material layer includes an emission layer, and the emission layer includes the compound. The method of claim 11,
The light emitting layer is an organic light emitting device further comprising a phosphorescent material or a delayed fluorescent compound. The method of claim 10,
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 10,
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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