KR20210148554A - 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 a compound represented by chemical formula 1. The compound according to at least one embodiment can improve efficiency, low driving voltage, and/or improve lifespan characteristics in the organic light emitting device.

Description

Compound and organic light emitting device comprising the same

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

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

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

KR 20160026661 A

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

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

[Formula 1]

In Formula 1,

Ar1 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

Ra to Rc, R1, R4, R5 and R8 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imid; amide group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R2, R3, R6 and R7 are the same as or different from each other, and each independently hydrogen; or deuterium,

n9 is an integer of 0 to 3, and when n9 is 2 or more, R9 of 2 or more are the same as or different from each other,

n10 is an integer of 0 to 4, and when n10 is 2 or more, R10 of 2 or more are the same as or different from each other.

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

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

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

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

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

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

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

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

As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group; nitrile group (-CN); nitro group; hydroxyl group; amino group; silyl group; boron group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group, is substituted with a substituent to which two or more of the above exemplified substituents are connected, or does not have any substituents. For example, "a substituent in which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which two phenyl groups are connected.

As used herein, the term "substituted or unsubstituted" refers to deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group, is substituted with a substituent to which two or more of the above-exemplified substituents are connected, or does not have any substituents.

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

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

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

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

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

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

In the present specification, the alkoxy group may be a straight chain, branched chain or cyclic chain. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C20. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, 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 is not limited thereto. .

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

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the carbon number of the alkenyl group is 2 to 20. According to another exemplary embodiment, the carbon number of the alkenyl group is 2 to 10. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but are not limited thereto.

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

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

In the present specification, the amine group is -NH ₂ , and the amine group may be substituted with the above-described alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, and combinations thereof. The number of carbon atoms of the substituted amine group is not particularly limited, but is preferably 1 to 30. According to an exemplary embodiment, the carbon number of the amine group is 1 to 20. According to an exemplary embodiment, the carbon number of the amine group is 1 to 10. Specific examples of the substituted amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a 9,9-dimethylfluorenylphenylamine group, a pyridylphenylamine group, and a diphenylamine group. group, phenylpyridylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, dibenzofuranylphenylamine group, 9-methylanthracenylamine group, diphenylamine group, phenylnaphthylamine group, There is a ditolylamine group, a phenyltolylamine group, a diphenylamine group, and the like, but is not limited thereto.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 30. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 20. The aryl group may be a monocyclic aryl group, such as a phenyl group, a biphenyl group, a terphenyl group, or a quaterphenyl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a triphenyl group, a chrysenyl group, a fluorenyl group, a triphenylenyl group, etc., but is not 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-dimethyl fluorenyl group), and

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

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

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

In the present specification, the description of the above-described 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, "ring" is a hydrocarbon ring; or a heterocyclic ring.

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

In the present specification, the meaning of forming a ring by bonding with adjacent groups means a substituted or unsubstituted aliphatic hydrocarbon ring by bonding with adjacent groups; A substituted or unsubstituted aromatic hydrocarbon ring; substituted or unsubstituted aliphatic heterocycle; substituted or unsubstituted aromatic heterocycle; Or it means to form a condensed ring thereof. The hydrocarbon ring means a ring consisting of only carbon and hydrogen atoms. The heterocycle means 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 heterocycle and the aromatic heterocycle may be monocyclic or polycyclic.

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

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

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

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

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

The compound represented by Formula 1 of the present invention may improve carrier injection and movement by increasing the dipole moment by including a tetracyclic condensed ring including N and C in the anthracene structure.

In particular, when anthracene is bonded to a benzene ring directly condensed with an N-containing ring, the electron donating ability for anthracene is greater than in the case where the anthracene is directly condensed, so that injection and movement of holes is improved, and thus the driving voltage and lifespan are improved. show the effect.

Additionally, when the compound represented by Formula 1 of the present invention includes deuterium, the efficiency and lifespan of the device are improved. Specifically, when hydrogen is replaced with deuterium, the chemical properties of the compound hardly change, but the physical properties of the deuterated compound change and the vibrational energy level is lowered. The compound substituted with deuterium can prevent a decrease in intermolecular van der Waals force or decrease in quantum efficiency due to collisions due to intermolecular vibration. C-D bonds may also improve the stability of the compound.

Accordingly, when the compound represented by Chemical Formula 1 is applied to an organic light emitting device, an organic light emitting device having high efficiency, low voltage and/or long lifespan can be obtained.

Hereinafter, Formula 1 will be described in detail.

[Formula 1]

In Formula 1,

Ar1 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

Ra to Rc, R1, R4, R5 and R8 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imid; amide group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R2, R3, R6 and R7 are the same as or different from each other, and each independently hydrogen; or deuterium,

n9 is an integer of 0 to 3, and when n9 is 2 or more, R9 of 2 or more are the same as or different from each other,

n10 is an integer of 0 to 4, and when n10 is 2 or more, R10 of 2 or more are the same as or different from each other.

In an exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted C 6 to C 60 aryl group; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

In an exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted C6-C20 aryl group; Or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

In an exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted aryl group.

In an exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted phenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted pyrene group; A substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; a substituted or unsubstituted naphthobenzofuran group; a substituted or unsubstituted naphthobenzothiophene group; Or a substituted or unsubstituted carbazole group.

In an exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted phenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted pyrene group; A substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; a substituted or unsubstituted naphthobenzofuran group; Or a substituted or unsubstituted carbazole group.

In an exemplary embodiment of the present specification, Ar1 is a phenyl group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; a naphthyl group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; a biphenyl group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; a phenanthrenyl group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; a triphenylene group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; a fluorenyl group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; a pyrene group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; a dibenzofuran group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; a dibenzothiophene group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; a naphthobenzofuran group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; Or a carbazole group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group.

In an exemplary embodiment of the present specification, Ar1 is a phenyl group unsubstituted or substituted with deuterium, a methyl group, a phenyl group, or a naphthyl group; a naphthyl group unsubstituted or substituted with deuterium, a methyl group, a phenyl group, or a naphthyl group; a biphenyl group unsubstituted or substituted with deuterium, a methyl group, a phenyl group, or a naphthyl group; a phenanthrenyl group unsubstituted or substituted with deuterium, a methyl group, a phenyl group, or a naphthyl group; a triphenylene group unsubstituted or substituted with deuterium, a methyl group, a phenyl group, or a naphthyl group; a fluorenyl group unsubstituted or substituted with deuterium, a methyl group, a phenyl group, or a naphthyl group; a pyrene group unsubstituted or substituted with deuterium, a methyl group, a phenyl group, or a naphthyl group; a dibenzofuran group unsubstituted or substituted with deuterium, a methyl group, a phenyl group, or a naphthyl group; a dibenzothiophene group unsubstituted or substituted with deuterium, a methyl group, a phenyl group, or a naphthyl group; a naphthobenzofuran group unsubstituted or substituted with deuterium, a methyl group, a phenyl group, or a naphthyl group; or a carbazole group unsubstituted or substituted with deuterium, a methyl group, a phenyl group, or a naphthyl group.

In an exemplary embodiment of the present specification, Ar1 is a phenyl group unsubstituted or substituted with any one of the group consisting of deuterium, a phenyl group and a naphthyl group, or a group to which two or more of the foregoing groups are connected; a naphthyl group unsubstituted or substituted with any one of the group consisting of deuterium, a phenyl group, and a naphthyl group, or a group to which two or more of the aforementioned groups are connected; biphenyl group; a phenanthrenyl group unsubstituted or substituted with any one of the group consisting of a phenyl group and a naphthyl group, or a group to which two or more of the aforementioned groups are connected; triphenylene group; a fluorenyl group unsubstituted or substituted with a methyl group; pyrene; dibenzofuran group; dibenzothiophene group; naphthobenzofuran group; Or a carbazole group unsubstituted or substituted with a phenyl group.

In an exemplary embodiment of the present specification, Ar1 is a phenyl group unsubstituted or substituted with deuterium, a phenyl group, or a naphthyl group; a naphthyl group unsubstituted or substituted with deuterium, a phenyl group, or a naphthyl group; biphenyl group; a phenanthrenyl group unsubstituted or substituted with a phenyl group or a naphthyl group; triphenylene group; a fluorenyl group unsubstituted or substituted with a methyl group; pyrene; dibenzofuran group; dibenzothiophene group; naphthobenzofuran group; Or a carbazole group unsubstituted or substituted with a phenyl group.

In an exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted phenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted dibenzofuran group.

In an exemplary embodiment of the present specification, Ar1 is a phenyl group unsubstituted or substituted with deuterium or a naphthyl group; a naphthyl group unsubstituted or substituted with deuterium; biphenyl group; or a dibenzofuran group.

In an exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted phenyl group; or a substituted or unsubstituted naphthyl group.

In an exemplary embodiment of the present specification, Ar1 is a phenyl group; or a naphthyl group.

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

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In Formulas 1-1 to 1-4, Ar1, R1 to R10, n9, and n10 have the same definitions as in Formula 1 above.

In an exemplary embodiment of the present specification, Ra to Rc, R1, R4, R5 and R8 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In an exemplary embodiment of the present specification, Ra to Rc, R1, R4, R5 and R8 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C 1 to C 60 alkyl group; a substituted or unsubstituted 6 to 60 aryl group; Or a substituted or unsubstituted 2 to 60 heterocyclic group.

In an exemplary embodiment of the present specification, Ra to Rc, R1, R4, R5 and R8 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C 1 to C 30 alkyl group; a substituted or unsubstituted 6 to 30 aryl group; Or a substituted or unsubstituted 2 to 30 heterocyclic group.

In an exemplary embodiment of the present specification, Ra to Rc, R1, R4, R5 and R8 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C 1 to C 20 alkyl group; a substituted or unsubstituted 6 to 20 aryl group; Or a substituted or unsubstituted 2 to 20 heterocyclic group.

In an exemplary embodiment of the present specification, Ra to Rc, R1, R4, R5 and R8 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

In an exemplary embodiment of the present specification, Ra to Rc, R1, R4, R5 and R8 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted methyl group; a substituted or unsubstituted phenyl group; or a substituted or unsubstituted naphthyl group.

In an exemplary embodiment of the present specification, Ra to Rc, R1, R4, R5 and R8 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; methyl group; phenyl group; or a naphthyl group.

In an exemplary embodiment of the present specification, Ra to Rc, R1, R4, R5 and R8 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; methyl group; or a phenyl group.

In an exemplary embodiment of the present specification, Ra and Rb are a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

In an exemplary embodiment of the present specification, Ra and Rb are a substituted or unsubstituted alkyl group.

In an exemplary embodiment of the present specification, Ra and Rb are substituted or unsubstituted methyl groups.

In an exemplary embodiment of the present specification, Ra and Rb are methyl groups.

In an exemplary embodiment of the present specification, Rc is a substituted or unsubstituted aryl group.

In an exemplary embodiment of the present specification, Rc is a substituted or unsubstituted C6-C30 aryl group.

In an exemplary embodiment of the present specification, Rc is a substituted or unsubstituted C6-C20 aryl group.

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

In an exemplary embodiment of the present specification, Rc is a phenyl group unsubstituted or substituted with deuterium.

In an exemplary embodiment of the present specification, Rc is a phenyl group.

In an exemplary embodiment of the present specification, R1, R4, R5 and R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted aryl group.

In an exemplary embodiment of the present specification, R1, R4, R5 and R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted aryl group.

In an exemplary embodiment of the present specification, R1, R4, R5 and R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a substituted or unsubstituted C6-C30 aryl group.

In an exemplary embodiment of the present specification, R1, R4, R5 and R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a substituted or unsubstituted C6-C20 aryl group.

In an exemplary embodiment of the present specification, R1, R4, R5 and R8 are the same as or different from each other, and each independently hydrogen; or deuterium.

In an exemplary embodiment of the present specification, R1, R4, R5 and R8 are hydrogen.

In an exemplary embodiment of the present specification, R1, R4, R5 and R8 are deuterium.

In an exemplary embodiment of the present specification, R2, R3, R6 and R7 are the same as or different from each other, and each independently hydrogen; or deuterium.

In an exemplary embodiment of the present specification, R2, R3, R6 and R7 are hydrogen.

In an exemplary embodiment of the present specification, R2, R3, R6 and R7 are deuterium.

In an exemplary embodiment of the present specification, R9 and R10 are the same as or different from each other, and each independently hydrogen; or deuterium.

In an exemplary embodiment of the present specification, R9 and R10 are hydrogen.

In an exemplary embodiment of the present specification, R9 and R10 are deuterium.

In the exemplary embodiment of the present specification, all hydrogens in Formula 1 may be substituted with deuterium.

In the 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, Ar1, R1 to R10, n9, and n10 have the same definitions as in Formula 1 above.

는 하기 구조식 중 어느 하나로 표시된다. 이때,

는 결합 위치를 의미한다.In one embodiment of the present specification, the formula (1)

is represented by any one of the following structural formulas. At this time,

denotes a binding position.

In the above structural formula, Rc is the same as defined in Formula 1 above.

는 하기 구조식 중 어느 하나로 표시된다. 이때,

는 결합 위치를 의미한다.In one embodiment of the present specification, the formula (1)

is represented by any one of the following structural formulas. At this time,

denotes a binding position.

In the above structural formula, Rc is the same as defined in Formula 1 above.

In the above structural formula, Rc is a substituted or unsubstituted aryl group.

In the above structural formula, Rc is a phenyl group.

In the exemplary embodiment of the present specification, n9 is 0.

In the exemplary embodiment of the present specification, n9 is an integer of 1 to 3.

In the exemplary embodiment of the present specification, n9 is 1.

In the exemplary embodiment of the present specification, n9 is 3.

In the exemplary embodiment of the present specification, n10 is 0.

In the exemplary embodiment of the present specification, n10 is an integer of 1 to 4.

In the exemplary embodiment of the present specification, n10 is 1.

In one embodiment of the present specification, n10 is 4.

In the exemplary embodiment of the present specification, Ar1 is substituted with at least one deuterium. In another exemplary embodiment, Ar1 is substituted by 40% or more with deuterium. In another exemplary embodiment, Ar1 is substituted by 50% or more with deuterium. In another exemplary embodiment, Ar1 is substituted by 60% or more with deuterium. In another exemplary embodiment, Ar1 is substituted with deuterium by 70% or more. In another exemplary embodiment, Ar1 is substituted by 80% or more with deuterium. In another exemplary embodiment, Ar1 is substituted by 90% or more with deuterium. In another exemplary embodiment, Ar1 is 100% substituted with deuterium.

는 적어도 하나의 중수소로 치환된다. 또 다른 일 실시상태에 있어서, 상기 치환기는 중수소로 40% 이상 치환된다. 또 다른 일 실시상태에 있어서, 상기 치환기는 중수소로 50% 이상 치환된다. 또 다른 일 실시상태에 있어서, 상기 치환기는 중수소로 60% 이상 치환된다. 또 다른 일 실시상태에 있어서, 상기 치환기는 중수소로 70% 이상 치환된다. 또 다른 일 실시상태에 있어서, 상기 치환기는 중수소로 80% 이상 치환된다. 또 다른 일 실시상태에 있어서, 상기 치환기는 중수소로 90% 이상 치환된다. 또 다른 일 실시상태에 있어서, 상기 치환기는 중수소로 100% 치환된다.In the exemplary embodiment of the present specification, the substituent of Formula 1

is substituted with at least one deuterium. In another exemplary embodiment, the substituent is substituted with deuterium by 40% or more. In another exemplary embodiment, the substituent is 50% or more substituted with deuterium. In another exemplary embodiment, the substituent is substituted with deuterium by 60% or more. In another exemplary embodiment, the substituent is 70% or more substituted with deuterium. In another exemplary embodiment, the substituent is 80% or more substituted with deuterium. In another exemplary embodiment, the substituent is substituted with deuterium by 90% or more. In another exemplary embodiment, the substituent is 100% substituted with deuterium.

In the exemplary embodiment of the present specification, each of Ra to Rc and R1 to R10 is substituted with at least one deuterium. In another exemplary embodiment, each of Ra to Rc and R1 to R10 is substituted by 40% or more with deuterium. In another exemplary embodiment, each of Ra to Rc and R1 to R10 is substituted by 50% or more with deuterium. In another exemplary embodiment, each of Ra to Rc and R1 to R10 is substituted with deuterium by 60% or more. In another exemplary embodiment, each of Ra to Rc and R1 to R10 is substituted with deuterium by 70% or more. In another exemplary embodiment, each of Ra to Rc and R1 to R10 is substituted by 80% or more with deuterium. In another exemplary embodiment, each of Ra to Rc and R1 to R10 is substituted by 90% or more with deuterium. In another exemplary embodiment, each of Ra to Rc and R1 to R10 is 100% substituted with deuterium.

In an exemplary embodiment of the present specification, the compound represented by Formula 1 is substituted with at least one deuterium. In another exemplary embodiment, the compound represented by Formula 1 is substituted with deuterium by 20% or more. In another exemplary embodiment, the compound represented by Formula 1 is substituted with deuterium by 30% or more. In another exemplary embodiment, the compound represented by Formula 1 is substituted with deuterium by 40% or more. In another exemplary embodiment, the compound represented by Formula 1 is substituted with deuterium by 50% or more. In another exemplary embodiment, the compound represented by Formula 1 is substituted with deuterium by 60% or more. In another exemplary embodiment, the compound represented by Formula 1 is substituted with deuterium by 70% or more. In another exemplary embodiment, the compound represented by Formula 1 is substituted with deuterium by 80% or more. In another exemplary embodiment, the compound represented by Formula 1 is substituted with deuterium by 90% or more. In another exemplary embodiment, the compound represented by Formula 1 is 100% substituted with deuterium.

In an exemplary embodiment of the present specification, 4 or more of R1 to R8 are deuterium, and the remainder is hydrogen. In another exemplary embodiment, 5 or more of R1 to R8 are deuterium, and the remainder is hydrogen. In another exemplary embodiment, 6 or more of R1 to R8 are deuterium, and the remainder is hydrogen. In another exemplary embodiment, at least 7 of R1 to R8 are deuterium, and the remainder is hydrogen. In another exemplary embodiment, R1 to R8 are all deuterium. In this case, the remaining substituents (Ra to Rc, Ar1, R9 and R10) other than R1 to R8 are unsubstituted or substituted with deuterium.

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

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

<Scheme 1>

In Scheme 1, X1 is N-Rc, X2 is CRaRb, and definitions of the remaining substituents are the same as those in Formula 1 above.

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

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

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

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

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

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

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

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

The organic material layer of the organic light emitting device of the present specification may have a single-layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention comprises at least one of a hole transport layer, a hole injection layer, an electron blocking layer, a hole transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron transport and injection layer as an organic material layer. It may have a structure containing However, the structure of the organic light emitting device of the present specification is not limited thereto and may include a smaller number or a larger number of organic material layers.

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

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

In an exemplary embodiment of the present specification, the organic material layer includes an electron injection layer, an electron transport layer, an electron injection and transport layer or a hole blocking layer, and the electron injection layer, the electron transport layer, the electron injection and transport layer or the hole blocking layer is the above-described The compound represented by Formula 1 may be included.

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

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

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

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

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

In the exemplary embodiment of the present specification, the organic light emitting device is a green organic light emitting device in which the light emitting layer includes the compound represented by Formula 1 as a host.

According to an exemplary embodiment of the present specification, the organic light emitting device is a red organic light emitting device in which the light emitting layer includes the compound represented by Formula 1 as a host.

In another exemplary embodiment, the organic light emitting device is a blue organic light emitting device in which the light emitting layer includes the compound represented by Formula 1 as a host.

In the exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound represented by Formula 1 as a host, and may further include a dopant. In this case, the content of the dopant may be included in an amount of 1 part by weight to 60 parts by weight, preferably 1 part by weight to 10 parts by weight, based on 100 parts by weight of the host.

In this case, as the dopant, a _{phosphorescent material such as (4,6-F2ppy) 2} Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), distrylarylene (DSA), PFO-based polymer, PPV-based polymer A fluorescent material such as a polymer, an anthracene-based compound, a pyrene-based compound, or a boron-based compound may be used, but is not limited thereto.

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

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

In the organic light emitting diode according to the exemplary embodiment of the present specification, the maximum emission peak of the organic material layer is 400 nm to 500 nm.

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

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

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

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

In an exemplary embodiment of the present specification, the light emitting layer including the compound represented by Formula 1 has a blue color.

According to an example, the content of the compound represented by Formula 1 is 70 parts by weight to 99.99 parts by weight based on 100 parts by weight of the total of the host and dopant of the emission layer; Preferably, 80 parts by weight to 99.9 parts by weight; More preferably, it is 90 parts by weight to 99.5 parts by weight.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

(4) anode / hole transport layer / light emitting layer / electron transport layer / cathode

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

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

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

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

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

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

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

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

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

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

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

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

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

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

1 illustrates a structure of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 5, and a cathode 8 are sequentially stacked. In such a structure, the compound may be included in the light emitting layer 6 .

Figure 2 is a substrate (1), anode (2), hole injection layer (3), hole transport layer (4), light emitting layer (5), electron transport layer (6), electron injection layer (7) and cathode (8) are sequentially The structure of the organic light-emitting device stacked with In such a structure, the compound may be included in the hole injection layer 3 , the hole transport layer 4 , the light emitting layer 5 , the electron transport layer 6 , or the electron injection layer 7 .

For example, the organic light emitting device according to the present specification uses a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to form a metal or a conductive metal oxide or an alloy thereof on a substrate. is deposited to form an anode, and an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, an electron transport layer and an electron injection layer is formed thereon, and then a material that can be used as a cathode is deposited thereon. can be In addition to this method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

The organic material layer may further include at least one of a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole transport and injection layer.

The organic material layer may have a multilayer structure including a hole injection layer, a hole transport layer, an electron injection and transport layer, an electron blocking layer, a light emitting layer and an electron transport layer, an electron injection layer, an electron transport and injection layer, etc., but is not limited thereto, and may have a single layer structure can In addition, the organic layer is formed using a variety of polymer materials in a smaller number by a solvent process rather than a vapor deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer method. It can be made in layers.

The anode is an electrode for injecting holes, and as the anode material, a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO, Indium Tin Oxide), and indium zinc oxide (IZO, Indium Zinc Oxide); ZnO: Al or SnO ₂ : Combination of metals and oxides such as Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

The cathode is an electrode for injecting electrons, and the cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; and a multi-layered material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

The hole injection layer is a layer that smoothly injects holes from the anode into the light emitting layer. As the hole injection material, holes can be well injected from the anode at a low voltage, and the highest occupied (HOMO) of the hole injection material is The molecular orbital) is preferably between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based organic material. of organic substances, anthraquinones, polyaniline and polythiophene-based conductive polymers, and the like, but are not limited thereto. The hole injection layer may have a thickness of 1 to 150 nm. When the thickness of the hole injection layer is 1 nm or more, there is an advantage in that the hole injection characteristics can be prevented from being deteriorated, and when it is 150 nm or less, the thickness of the hole injection layer is too thick, so that the driving voltage is increased to improve hole movement There are advantages to avoiding this.

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

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

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

The light emitting layer may emit red, green, or blue light, and may be made of a phosphorescent material or a fluorescent material. The light emitting material is a material capable of emitting light in the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include the aforementioned compound of Formula 1; 8-hydroxy-quinoline aluminum complex (Alq ₃ ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene, rubrene, and the like, but is not limited thereto.

Examples of the host material for the light emitting layer include a condensed aromatic ring derivative or a heterocyclic compound containing compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

When the emission layer emits red light, the emission dopant is PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium) ), a phosphorescent material such as octaethylporphyrin platinum (PtOEP), or a _{fluorescent material such as Alq 3} (tris(8-hydroxyquinolino)aluminum) may be used, but is not limited thereto. When the emission layer emits green light, a _{phosphor such as Ir(ppy) 3} (fac tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq3 (tris(8-hydroxyquinolino)aluminum) may be used as the emission dopant. However, the present invention is not limited thereto. When the light emitting layer emits blue light, the light emitting dopant includes a _{phosphorescent material such as (4,6-F2ppy) 2} Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), distrylarylene (DSA), A fluorescent material such as a PFO-based polymer or a PPV-based polymer may be used, but is not limited thereto.

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

The electron transport layer may serve to facilitate the 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 electron mobility is suitable. Specific examples include the above-mentioned compound or 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 in that the electron transport characteristics can be prevented from being deteriorated, and if it is 50 nm or less, the thickness of the electron transport layer is too thick to prevent an increase in the driving voltage to improve the movement of electrons. There are advantages that can be

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

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-crezolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. However, the present invention is not limited thereto.

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

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

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

Synthesis Example 1: Synthesis of intermediate a

Synthesis Example 1-1) Synthesis of intermediate a-1

3,3-dimethyl-2,3-dihydro-1H-inden-1-one (30 g, 187 mmol) and (4-bromophenyl) hydrazine (35 g, 187 mmol) were added to 300 ml of acetic acid, and at 80° C. for 12 hours stirred for a while. After removing the acetic acid, it is put in chloroform and extracted several times with water. The organic layer was treated with anhydrous magnesium sulfate, distilled under reduced pressure to remove chloroform, and purified by column chromatography to obtain an intermediate a-1. (32 g, yield 55%)

Synthesis Example 1-2) Synthesis of intermediate a-2

Intermediate a-1 (32g, 102mmol) and iodobenzene (20.9g, 102mml) were dissolved in DMF (dimethylformamide, dimethylformamide) 300ml, CS ₂ CO ₃ (66.8g, 205mmol) and CuI (3.90g, 20mmol) ) is put in. After raising the temperature to 120 ℃ stirred for 16 hours. After cooling the reaction solution, 1 L of ethyl acetate is added, transferred to a separatory funnel, extracted once with aqueous ammonia, and extracted 3 times with 1 L of distilled water. The organic layers were collected, treated with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. Purification using column chromatography (eluent EA:Hex) to obtain intermediate a-2. (25g, yield 63%)

Synthesis Example 1-3) Synthesis of intermediate a

Intermediate a-2 (25g, 64mmol), bis(pinacolato)diboron (19.6g, 77mmol), and KOAc (12.6g, 128mmol) were put in a flask together with 200ml of Dioxane and dispersed. After adding Pd(dba) ₂ (0.74 g, 1.3 mmol) and PCy ₃ (0.72 g, 2.6 mmol), the mixture was stirred under reflux for 24 hours. After completion of the reaction, dioxane is removed by distillation under reduced pressure. After dissolving in chloroform and extracting with distilled water three times, the organic layer was distilled under reduced pressure to remove chloroform and purified using column chromatography to obtain an intermediate a. (20g, yield 71%)

Synthesis Example 2: Synthesis of intermediates b and c

Synthesis Example 2-1) Synthesis of intermediates b-1 and c-1

In Synthesis Example 1-1, except that (3-bromophenyl) hydrazine was used instead of (4-bromophenyl) hydrazine, it was synthesized in the same manner and purified through column chromatography to obtain intermediates b-1 and c-1 It is obtained in a ratio of about 5:1.

Synthesis Example 2-2) Synthesis of intermediate b-2

In Synthesis Example 1-2, an intermediate b-2 was obtained by the same synthesis except that b-1 was used instead of intermediate a-1.

Synthesis Example 2-3) Synthesis of intermediate b

In Synthesis Example 1-3, an intermediate b was obtained by the same synthesis except that b-2 was used instead of intermediate a-2.

Synthesis Example 2-4) Synthesis of intermediate c-2

In Synthesis Example 1-2, the intermediate c-2 was obtained by the same synthesis except that c-1 was used instead of the intermediate a-1.

Synthesis Example 2-5) Synthesis of intermediate c

In Synthesis Example 1-3, an intermediate c was obtained by the same synthesis except that c-2 was used instead of intermediate a-2.

Synthesis Example 3: Synthesis of intermediate d

Synthesis Example 3-1) Synthesis of intermediate d-1

In Synthesis Example 1-1, (2-bromophenyl) hydrazine was used instead of (4-bromophenyl) hydrazine, and the same was synthesized to obtain an intermediate d-1.

Synthesis Example 3-2) Synthesis of intermediate d-2

In Synthesis Example 1-2, an intermediate d-2 was obtained by the same synthesis except that d-1 was used instead of intermediate a-1.

Synthesis Example 3-3) Synthesis of intermediate d

In Synthesis Example 1-3, an intermediate d was obtained by the same synthesis except that d-2 was used instead of intermediate a-2.

Synthesis Example 4: Synthesis of Intermediate e

Synthesis Example 4-1) Synthesis of Intermediate e-1

Except for using 1,1-dimethyl-1,3-dihydro-2H-inden-2-one instead of 3,3-dimethyl-2,3-dihydro-1H-inden-1-one in Synthesis Example 1-1 and synthesized in the same manner to obtain an intermediate e-1.

Synthesis Example 4-2) Synthesis of Intermediate e-2

In Synthesis Example 1-2, an intermediate e-2 was obtained by the same synthesis except that e-1 was used instead of intermediate a-1.

Synthesis Example 4-3) Synthesis of Intermediate e

In Synthesis Example 1-3, an intermediate e was obtained by the same synthesis except that e-2 was used instead of intermediate a-2.

Synthesis Example 5: Synthesis of intermediates f and g

Synthesis Example 5-1) Synthesis of intermediates f-1 and g-1

1,1-dimethyl-1,3-dihydro-2H-inden-2-one instead of 3,3-dimethyl-2,3-dihydro-1H-inden-1-one in Synthesis Example 1-1, ( Except that (3-bromophenyl) hydrazine was used instead of 4-bromophenyl) hydrazine, Intermediate f-1 and Intermediate g-1 produced by the same synthesis were obtained by separating through column chromatography.

Synthesis Example 5-2) Synthesis of intermediate f-2

In Synthesis Example 1-2, an intermediate f-2 was obtained by the same synthesis except that f-1 was used instead of intermediate a-1.

Synthesis Example 5-3) Synthesis of intermediate f

In Synthesis Example 1-3, an intermediate f was obtained by the same synthesis except that f-2 was used instead of intermediate a-2.

Synthesis Example 5-4) Synthesis of Intermediate g-2

In Synthesis Example 1-2, an intermediate g-2 was obtained by the same synthesis except that g-1 was used instead of intermediate a-1.

Synthesis Example 5-5) Synthesis of intermediate g

In Synthesis Example 1-3, an intermediate g was obtained by the same synthesis except that g-2 was used instead of intermediate a-2.

Synthesis Example 6: Synthesis of intermediate h

Synthesis Example 6-1) Synthesis of intermediate h-1

1,1-dimethyl-1,3-dihydro-2H-inden-2-one instead of 3,3-dimethyl-2,3-dihydro-1H-inden-1-one in Synthesis Example 1-1, ( Intermediate h-1 was obtained by the same synthesis except that (2-bromophenyl)hydrazine was used instead of 4-bromophenyl)hydrazine.

Synthesis Example 6-2) Synthesis of intermediate h-2

In Synthesis Example 1-2, an intermediate h-2 was obtained by the same synthesis except that h-1 was used instead of intermediate a-1.

Synthesis Example 6-3) Synthesis of intermediate h

In Synthesis Example 1-3, an intermediate h was obtained by the same synthesis except that h-2 was used instead of intermediate a-2.

Synthesis Example 7: Synthesis of compound 1

After dissolving 9-bromo-10-phenylanthracene (15 g, 45 mmol) and intermediate a (19.6 g, 45 mmol) in Dioxane (200 ml), Pd (PPh ₃ ) ₄ (1.04 g, 0.7 mmol) and 2M K ₂ 50ml of CO ₃ aqueous solution was added and stirred under reflux for 24 hours. After cooling the reaction solution, the organic layer was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The organic solvent was removed under reduced pressure and purified using column chromatography to obtain compound 1 (19 g, yield 75%). [M+H ⁺ ]= 562.3

Synthesis Example 8: Synthesis of compound 2

In Synthesis Example 7, 9-bromo-10-(naphthalen-1-yl)anthracene was used instead of 9-bromo-10-phenylanthracene, and Intermediate b was used instead of Intermediate a to obtain compound 2 . [M+H ⁺ ]= 612.3

Synthesis Example 9: Synthesis of compound 3

In Synthesis Example 7, 9-bromo-10-(naphthalen-2-yl)anthracene was used instead of 9-bromo-10-phenylanthracene, and Intermediate c was used instead of Intermediate a to obtain compound 3 . [M+H ⁺ ]= 612.3

Synthesis Example 10: Synthesis of compound 4

Except for using 9-([1,1'-biphenyl]-4-yl)-10-bromoanthracene instead of 9-bromo-10-phenylanthracene in Synthesis Example 7, and intermediate d instead of intermediate a Compound 4 was obtained through the same synthesis. [M+H ⁺ ]= 638.3

Synthesis Example 11: Synthesis of compound 5

Except for using 9-([1,1'-biphenyl]-3-yl)-10-bromoanthracene instead of 9-bromo-10-phenylanthracene in Synthesis Example 7 and intermediate e instead of intermediate a Compound 5 was obtained through the same synthesis. [M+H ⁺ ]= 638.3

Synthesis Example 12: Synthesis of compound 6

In Synthesis Example 7, 9-([1,1'-biphenyl]-2-yl)-10-bromoanthracene was used instead of 9-bromo-10-phenylanthracene, and the intermediate f was used instead of the intermediate a. Compound 6 was obtained through the same synthesis. [M+H ⁺ ]= 638.3

Synthesis Example 13: Synthesis of compound 7

Synthesis Example 13-1) Synthesis of compound 7-1

After dissolving 9-bromoanthracene (30 g, 117 mmol) and (3- (naphthalen-1-yl) phenyl) boronic acid (28.9 g, 117 mmol) in Dioxane (600 ml), Pd (PPh3) 4 (2.69 g, 2.33 mmol) and 150 ml of 2M K2CO3 aqueous solution were added and stirred under reflux for 24 hours. After cooling the reaction solution, the organic layer was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The organic solvent was removed under reduced pressure and purified using column chromatography to obtain compound 7-1 (31 g, yield 74%).

Synthesis Example 13-2) Synthesis of compound 7-2

Compound 7-1 (31 g, 86 mmol) was dissolved in 400 ml of DMF, and then N-bromosuccinimide (15.3 g, 86 mmol) dissolved in 50 ml of DMF was slowly added dropwise. After stirring at room temperature for 2 hours, 300 ml of water was added dropwise. When a solid is formed, it is dissolved in chloroform after filtering and extracted several times with distilled water. Recrystallization from ethyl acetate gave compound 7-2. (27 g, yield 68%)

Synthesis Example 13-3) Synthesis of compound 7

Compound 7 was obtained by the same synthesis, except that in Synthesis Example 7, compound 7-2 was used instead of 9-bromo-10-phenylanthracene, and intermediate g was used instead of intermediate a. [M+H ⁺ ]= 688.3

Synthesis Example 14: Synthesis of compound 8

Synthesis Example 14-1) Synthesis of compound 8-1

Compound 8-1 was obtained by the same synthesis except that dibenzo[b,d]furan-2-ylboronic acid was used instead of (3-(naphthalen-1-yl)phenyl)boronic acid in Synthesis Example 13-1.

Synthesis Example 14-2) Synthesis of compound 8-2

In Synthesis Example 13-2, compound 8-2 was obtained by the same synthesis except that compound 8-1 was used instead of compound 7-1.

Synthesis Example 14-3) Synthesis of compound 8

Compound 8 was obtained by the same synthesis as in Synthesis Example 7, except that compound 8-2 was used instead of 9-bromo-10-phenylanthracene, and intermediate h was used instead of intermediate a. [M+H ⁺ ]= 652.3

Synthesis Example 15: Synthesis of compound 9

Compound 1 (10g) and AlCl ₃ (2g) were _{added to C 6} D ₆ (200ml) and stirred for 2 hours. After completion of the reaction, D ₂ O (15ml) was added, stirred for 30 minutes, and then trimethylamine (1.2ml) was added dropwise. The reaction solution was transferred to a separatory funnel, and extracted with water and toluene. The extract _{was dried over MgSO 4} , and recrystallized from ethyl acetate to obtain compound 9. (7.8 g, yield 78%) [M+H ⁺ ]=587.4

Synthesis Example 16: Synthesis of compound 10

Compound 10 was obtained by the same synthesis, except that Compound 2 was used instead of Compound 1 in Synthesis Example 15. [M+H ⁺ ]=639.4

Example 1

A glass substrate coated with indium tin oxide (ITO) to a thickness of 150 nm was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a product manufactured by Fischer Co. was used as the detergent, and distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water. After washing ITO for 30 minutes, ultrasonic cleaning was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, and after drying, it was transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using nitrogen plasma, the substrate was transported to a vacuum evaporator. On the thus prepared ITO transparent electrode, the following HAT-CN compound was thermally vacuum deposited to a thickness of 5 nm to form a hole injection layer. Then, HTL1 was thermally vacuum deposited to a thickness of 100 nm, and then HTL2 was thermally vacuum deposited to a thickness of 10 nm to form a hole transport layer. Then, compound 1 as a host and BD-A (weight ratio 95:5) as a dopant were simultaneously vacuum-deposited to form a light emitting layer with a thickness of 20 nm. Then, ETL was vacuum-deposited to a thickness of 20 nm to form an electron transport layer. Then, LiF was vacuum-deposited to a thickness of 0.5 nm to form an electron injection layer. Then, aluminum was deposited to a thickness of 100 nm to form a cathode, thereby manufacturing an organic light emitting diode.

The structures of the compounds used in the Examples are as follows.

Examples 2 to 10 and Comparative Examples 1 to 4

An organic light emitting diode was manufactured in the same manner as in Example 1, except that the compounds shown in Table 1 were used instead of Compound 1 as the host of the light emitting layer. At this time, among the following structures, the compound represented by Formula 1 of the present invention was prepared through the same process as in Synthesis Examples 1 to 16, respectively.

In the organic light emitting devices prepared in Examples 1 to 10 and Comparative Examples 1 to 4, the driving voltage and luminous efficiency were measured at a current density of ^{10 mA/cm 2} , and initial luminance at a current density of ^{20 mA/cm 2} The time (LT) to be 95% of the contrast was measured, and the results are shown in Table 1 below.

compound
(light emitting layer host) 10 mA/cm ² measured value LT (T95%) Vop Cd/A Example 1 compound 1 4.02 6.60 181 Example 2 compound 2 4.01 6.80 183 Example 3 compound 3 4.09 6.77 175 Example 4 compound 4 4.15 6.72 190 Example 5 compound 5 4.03 6.75 169 Example 6 compound 6 4.10 6.67 180 Example 7 compound 7 4.13 6.80 188 Example 8 compound 8 3.99 6.90 167 Example 9 compound 9 4.03 6.58 270 Example 10 compound 10 4.02 6.82 263 Comparative Example 1 BH-A 4.61 6.12 112 Comparative Example 2 BH-B 4.40 5.51 125 Comparative Example 3 BH-C 4.22 6.40 129 Comparative Example 4 BH-D 4.21 6.37 122

All of Examples 1 to 10 using the compound represented by Formula 1 of the present invention exhibited characteristics of low voltage and high efficiency, and showed superior lifespan compared to Comparative Examples 1 to 4. In particular, Examples 11 and 12 showed that the lifetime was further improved by deuterium substitution.

Comparative Example 1 using a host compound consisting only of aryl had a high driving voltage and was not advantageous in terms of efficiency and lifetime, and Comparative Example 2 and Comparative Example 2 using a host compound containing a dibenzofuran group and anthracene on the benzene ring not directly condensed with the N-containing ring In Comparative Examples 3 and 4 using the combined compound, it was confirmed that the driving voltage was higher than in Examples 1 to 10 and not advantageous in terms of efficiency and lifespan.

Although the preferred embodiment (host) of the present invention has been described above, the present invention is not limited thereto, and various modifications can be made within the scope of the claims and detailed description of the invention, and this also belong to the category

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

Claims (12)

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

In Formula 1,
Ar1 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
Ra to Rc, R1, R4, R5 and R8 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imid; amide group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted boron group; a substituted or unsubstituted amine group; a substituted or unsubstituted arylphosphine group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
R2, R3, R6 and R7 are the same as or different from each other, and each independently hydrogen; or deuterium,
n9 is an integer of 0 to 3, and when n9 is 2 or more, R9 of 2 or more are the same as or different from each other,
n10 is an integer from 0 to 4, and when n10 is 2 or more, R10 of 2 or more are the same as or different from each other. The method according to claim 1, wherein Formula 1 is a compound represented by any one of the following Formulas 1-1 to 1-4:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In Formulas 1-1 to 1-4, Ar1, R1 to R10, n9, and n10 have the same definitions as in Formula 1 above. The method according to claim 1, wherein Chemical Formula 1 is a compound represented by the following Chemical Formula 2-1 or 2-2:
[Formula 2-1]

[Formula 2-2]

In Formulas 2-1 and 2-2, Ar1, R1 to R10, n9, and n10 have the same definitions as in Formula 1 above. The compound of claim 1, wherein Ra and Rb are a substituted or unsubstituted alkyl group. The method according to claim 1, wherein R9 and R10 are the same as or different from each other, and each independently hydrogen; or deuterium. The method according to claim 1, wherein R1, R4, R5 and R8 are the same as or different from each other, and each independently hydrogen; or deuterium. The compound according to claim 1, wherein Formula 1 is represented by any one of the following compounds:

. anode; cathode; and at least one organic material layer provided between the anode and the cathode, wherein at least one of the organic material layers comprises the compound according to any one of claims 1 to 7. 9. The method of claim 8,
The organic material layer includes an emission layer, and the emission layer includes the compound. The organic light emitting diode of claim 9 , wherein the emission layer includes the compound as a host and further includes a dopant. 9. The method of claim 8,
The organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer is an organic light emitting device that includes the compound. 9. The method of claim 8,
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 includes the compound.

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