KR20220013316A - Compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification relates to a compound of chemical formula 1 and an organic light emitting device including the same. The compound according to an exemplary embodiment of the present specification can be used as a material for an organic material layer of the organic light emitting device, and by using the same, it is possible to improve efficiency, lower driving voltage, and/or improve lifespan characteristics in the organic light emitting device.

Description

Compound and organic light emitting device including the same

This application claims the benefit of the filing date of Korean Patent Application No. 10-2020-0092277, filed with the Korean Intellectual Property Office on July 24, 2020, the entire contents of which are incorporated herein by reference.

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. In the structure of the organic light emitting device, when a voltage is applied between the two electrodes, holes are injected into the organic material layer from the anode and electrons from the cathode are injected into the organic material layer. When the injected holes and electrons meet, excitons are formed, and the excitons When it falls back to the ground state, it lights up.

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

US Patent Application Publication No. 2004-0251816

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,

X1 is O or S;

At least one of Y1 to Y5 is N, and the others are each independently CR3,

R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group, may be combined with each other to form a substituted or unsubstituted aliphatic hydrocarbon ring,

R3 is hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group including a 6-membered ring including N; Or a substituted or unsubstituted, O, or a heteroaryl group containing S, or may combine with an adjacent group to form a substituted or unsubstituted ring,

L1 is a direct bond; a substituted or unsubstituted alkylene group; a substituted or unsubstituted alkenylene group; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

l1 is an integer from 1 to 5,

m is 1 or 2,

n is an integer from 1 to 4,

When l1 is 2 or more, the 2 or more L1s are the same as or different from each other,

는 서로 같거나 상이하고,When n is 2 or more, the 2 or more

are the same as or different from each other,

는 상기 L1이 화학식 1에 결합되는 부위를 의미한다.

denotes a site at which L1 is bonded to Formula 1.

In addition, an exemplary embodiment of the present specification includes a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound.

The compound according to an exemplary embodiment of the present specification may be used as a material of an organic material layer of an organic light emitting device, and by using it, it is possible to improve efficiency, low driving voltage and/or lifespan characteristics in an organic light emitting device.

1 and 2 show an example of an organic light emitting device according to an exemplary embodiment of the present specification.

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

The present specification provides a compound represented by Formula 1 above.

Formula 1 according to an exemplary embodiment of the present specification is a structure in which a cyano group and an N-containing monocyclic heterocyclic group derivative substituent are bonded to the xanthene or thioxanthene core, respectively, and is included in the organic material layer of the organic light emitting device to improve efficiency, low driving voltage and It is possible to improve the lifespan characteristics.

Specifically, since the N-containing heterocyclic group derivative and the cyano group of Formula 1 have an electron depletion structure, the dipole moment of a molecule can be increased. By smoothly controlling the electron mobility at the time, the efficiency and lifespan of the organic light emitting device including the compound represented by Formula 1 can be improved.

In addition, the steric hindrance due to the structure of xanthene and thioxanthene of the compound of Formula 1 prevents crystallization occurring during film formation, and maintains high thermal stability, so that it has a very stable effect even at a high deposition temperature. Accordingly, in the organic light emitting device including the compound according to the exemplary embodiment of the present specification, it is possible to improve efficiency, lower driving voltage, and improve lifespan characteristics.

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

는 연결되는 부위를 의미한다.In this specification,

means the part to be connected.

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

As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group; cyano group; an alkyl group; cycloalkyl group; alkoxy group; alkenyl group; haloalkyl group; silyl group; boron group; amine group; aryl group; And it means that it is substituted with one or more substituents selected from the group consisting of a heteroaryl group, is substituted with a substituent to which two or more of the above-exemplified substituents are connected, or does not have any substituents.

또는

의 치환기가 될 수 있다. 또한, 3개의 치환기가 연결되는 것은 (치환기 1)-(치환기 2)-(치환기 3)이 연속하여 연결되는 것뿐만 아니라, (치환기 1)에 (치환기 2) 및 (치환기 3)이 연결되는 것도 포함한다. 예컨대, 페닐기, 나프틸기 및 이소프로필기가 연결되어

,

, 또는

의 치환기가 될 수 있다. 4 이상의 치환기가 연결되는 것에도 전술한 정의가 동일하게 적용된다.In the present specification, that two or more substituents are connected means that hydrogen of any one substituent is connected with another substituent. For example, when two substituents are connected, a phenyl group and a naphthyl group are connected.

or

It can be a substituent of In addition, when three substituents are connected, (substituent 1)-(substituent 2)-(substituent 3) is not only continuously connected, but also (substituent 2) and (substituent 3) are connected to (substituent 1) include For example, a phenyl group, a naphthyl group and an isopropyl group are connected

,

, or

It can be a substituent of The above definition applies equally to a case in which 4 or more substituents are connected.

In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.

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 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, and specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, There are 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and adamantyl groups. , but is not limited thereto.

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-C30. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n -hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. may be It is not limited.

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 30. 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 is not limited thereto.

In the present specification, the haloalkyl group means that at least one halogen group is substituted for hydrogen in the alkyl group in the definition of the alkyl group.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.

When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, and the like, but is not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferable that it is C10-30. Specifically, the polycyclic aryl group may be a naphthyl group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a phenalene group, a perylene group, a chrysene group, a fluorene group, and the like, but is not limited thereto.

In the present specification, the fluorene group may be substituted, and adjacent groups may combine with each other to form a ring.

등이 있으나, 이에 한정되지 않는다.When the fluorene group is substituted,

and the like, but is not limited thereto.

As used herein, "adjacent" group means a substituent substituted on an atom directly connected to the atom in which the substituent is substituted, a substituent sterically closest to the substituent, or another substituent substituted on the atom in which the substituent is substituted. can For example, two substituents substituted at an ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as "adjacent" groups.

In the present specification, the heteroaryl group includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se and S, and the like. The number of carbon atoms is not particularly limited, but preferably has 2 to 30 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heterocyclic group include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a pyridine group, a bipyridine group, a pyrimidine group, a triazine group, a triazole group, an acridine group. , pyridazine group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, pyrido pyrimidine group, pyrido pyrazine group, pyrazino pyrazine group, isoquinoline group, indole group, carbazole group, benz Oxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuran group, phenanthridine group, phenanthroline group, isoxazole group, thia Diazole group, dibenzofuran group, dibenzosilol group, phenoxanthine group (phenoxathiine), phenoxazine group (phenoxazine), phenothiazine group (phenothiazine), dihydroindenocarbazole group, spirofluorene xanthene group and spirofluorene There is a thioxanthene group, but is not limited thereto.

In the present specification, the silyl group may be an alkylsilyl group, an arylsilyl group, a heteroarylsilyl group, or the like. Examples of the above-described alkyl group may be applied to the alkyl group of the alkylsilyl group, the examples of the aryl group may be applied to the aryl group of the arylsilyl group, and the heteroaryl group of the heteroarylsilyl group is an example of the heteroaryl group. can be applied.

In the present specification, the boron group may be -BR ₁₀₀ R ₁₀₁ , wherein R ₁₀₀ and R ₁₀₁ are the same or different, and each independently hydrogen; heavy hydrogen; halogen; nitrile group; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted C1-C30 linear or branched alkyl group; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And it may be selected from the group consisting of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms. The boron group specifically includes, but is not limited to, a dimethyl boron group, a diethyl boron group, a t-butylmethyl boron group, and a diphenyl boron group.

In the present specification, the amine group is -NH ₂ , an alkylamine group, an N-alkylarylamine group, an arylamine group, an N-arylheteroarylamine group, an N-alkylheteroarylamine group, and a heteroarylamine group from the group consisting of may be selected, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, and a 9-methyl-anthracenylamine group. , diphenylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, N-biphenylnaphthylamine group; N-naphthylfluorenylamine group, N-phenylphenanthrenylamine group, N-biphenylphenanthrenylamine group, N-phenylfluorenylamine group, N-phenylterphenylamine group, N-phenanthre There is a nylfluorenylamine group, an N-biphenylfluorenylamine group, and the like, but is not limited thereto.

In the present specification, the N-alkylarylamine group refers to an amine group in which an alkyl group and an aryl group are substituted with N of the amine group. The alkyl group and the aryl group in the N-alkylarylamine group are the same as the examples of the alkyl group and the aryl group described above.

In the present specification, the N-arylheteroarylamine group refers to an amine group in which an aryl group and a heteroaryl group are substituted with N of the amine group. The aryl group and the heteroaryl group in the N-arylheteroarylamine group are the same as the examples of the above-described aryl group and heteroaryl group.

In the present specification, the N-alkylheteroarylamine group refers to an amine group in which an alkyl group and a heteroaryl group are substituted with N of the amine group. The alkyl group and the heteroaryl group in the N-alkylheteroarylamine group are the same as the examples of the above-described alkyl group and heteroaryl group.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, or a substituted or unsubstituted diarylamine group. The arylamine group including two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time. For example, the aryl group in the arylamine group may be selected from the examples of the aryl group described above.

In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, or a substituted or unsubstituted diheteroarylamine group. The heteroarylamine group including two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group at the same time. For example, the heteroaryl group in the heteroarylamine group may be selected from the examples of the heteroaryl group described above.

In the present specification, among the substituents, "adjacent groups combine with each other to form a ring" means a substituted or unsubstituted hydrocarbon ring by combining adjacent groups with each other; Or it means to form a substituted or unsubstituted heterocyclic ring. For example, in Formula 1, when Y2 and Y3 are each independently CR3, each R3 may be an "adjacent group". Further, when Y1 is CR3, R3 and L1 may be "adjacent groups".

In the present specification, in a substituted or unsubstituted ring formed by bonding to each other, "ring" is a substituted or unsubstituted hydrocarbon ring; Or it means a substituted or unsubstituted heterocyclic ring.

In the present specification, the hydrocarbon ring may be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a condensed ring of an aromatic hydrocarbon and an aliphatic hydrocarbon, and may be selected from among the examples of the cycloalkyl group or the aryl group except for those not monovalent.

In the present specification, the heterocycle includes atoms other than carbon and one or more heteroatoms, and specifically, the heterocyclic atoms may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like. The heterocycle may be monocyclic or polycyclic, and may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and the aromatic heterocycle may be selected from examples of the heteroaryl group except that it is not monovalent.

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 alkylene group means that the alkyl group has two bonding positions, that is, a divalent group. Except that each of these groups is a divalent group, the description of the above-described alkyl group may be applied.

In the present specification, the alkenylene group means that the alkenyl group has two bonding sites, that is, a divalent group. The description of the alkenyl group described above may be applied, except that each of these groups is a divalent group.

In the present specification, the arylene group means that the aryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aryl group described above may be applied.

In the present specification, the heteroarylene group means that the heteroaryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the heteroaryl group described above may be applied.

Hereinafter, the compound represented by Formula 1 will be described in detail.

According to an exemplary embodiment of the present specification, X1 is O.

According to an exemplary embodiment of the present specification, X1 is S.

According to an exemplary embodiment of the present specification, Formula 1 is represented by Formula 2 or 3 below.

[Formula 2]

[Formula 3]

In Formulas 2 and 3,

R1, R2, Y1 to Y5, L1, 11, m, and n are the same as defined in Formula 1 above.

According to an exemplary embodiment of the present specification, m is 1.

According to an exemplary embodiment of the present specification, m is 2.

According to an exemplary embodiment of the present specification, n is 1.

According to an exemplary embodiment of the present specification, n is 2.

According to an exemplary embodiment of the present specification, n is 3.

According to an exemplary embodiment of the present specification, n is 4.

According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by Chemical Formula 4 or 5 below.

[Formula 4]

[Formula 5]

In Formulas 4 and 5,

X1, R1, R2, Y1 to Y5, L1 and 11 are the same as defined in Formula 1 above.

According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of Chemical Formulas 6 to 9 below.

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

In Formulas 6 to 9,

R1, R2, Y1 to Y5, L1 and 11 are the same as defined in Formula 1 above.

According to an exemplary embodiment of the present specification, l1 is 1.

According to an exemplary embodiment of the present specification, l1 is 2.

According to an exemplary embodiment of the present specification, l1 is 3.

In the present specification, in Formula 1, when l1 is 2 or more, two or more L1s are the same as or different from each other, and each L1 means that they are connected in series. For example, when l1 is 3 and L1 is a phenylene group, a naphthylene group, and a phenylene group, respectively, they may be connected as follows, but are not limited thereto, and the order or connection position of each L1 may be different.

은 예컨대, 상기 l1가 3인 경우, 상기 예시된 구조에서 세번째 위치한 말단의 치환기 즉, 페닐렌기에 결합되는 것을 의미한다.In addition, the formula (1)

For example, when l1 is 3, it means that it is bonded to a substituent at the third position in the structure, that is, a phenylene group.

According to an exemplary embodiment of the present specification, at least one of Y1 to Y5 is N, and the rest are each independently CR3.

According to an exemplary embodiment of the present specification, at least two of Y1 to Y5 are N, and the rest are each independently CR3.

According to an exemplary embodiment of the present specification, at least three of Y1 to Y5 are N, and the rest are each independently CR3.

According to an exemplary embodiment of the present specification, any one of Y1 to Y5 is N, and the others are each independently CR3.

According to an exemplary embodiment of the present specification, any two of Y1 to Y5 are N, and the rest are each independently CR3.

According to an exemplary embodiment of the present specification, any three of Y1 to Y5 are N, and the rest are each independently CR3.

According to an exemplary embodiment of the present specification, Y1 is N, Y2 to Y5 are the same as or different from each other, and are each independently CR3.

According to an exemplary embodiment of the present specification, Y2 is N, Y1 and Y3 to Y5 are the same as or different from each other, and are each independently CR3.

According to an exemplary embodiment of the present specification, Y3 is N, Y1, Y2, Y4 and Y5 are the same as or different from each other, and each independently represents CR3.

According to an exemplary embodiment of the present specification, Y1 and Y5 are N, Y2 to Y4 are the same as or different from each other, and each independently represents CR3.

According to an exemplary embodiment of the present specification, Y1 and Y3 are N, Y2, Y4 and Y5 are the same as or different from each other, and are each independently CR3.

According to an exemplary embodiment of the present specification, Y2 and Y4 are N, Y1, Y3 and Y5 are the same as or different from each other, and are each independently CR3.

According to an exemplary embodiment of the present specification, Y3 and Y5 are N, Y1, Y2 and Y4 are the same as or different from each other, and are each independently CR3.

According to an exemplary embodiment of the present specification, Y1 and Y2 are N, Y3 to Y5 are the same as or different from each other, and each independently represents CR3.

According to an exemplary embodiment of the present specification, Y4 and Y5 are N, Y1 to Y3 are the same as or different from each other, and are each independently CR3.

According to an exemplary embodiment of the present specification, Y2 and Y3 are N, Y1, Y4 and Y5 are the same as or different from each other, and are each independently CR3.

According to an exemplary embodiment of the present specification, Y3 and Y4 are N, Y1, Y2 and Y5 are the same as or different from each other, and are each independently CR3.

According to an exemplary embodiment of the present specification, Y1, Y3 and Y5 are N, Y2 and Y4 are the same as or different from each other, and are each independently CR3.

는 하기 구조 중에서 선택되는 어느 하나이다.According to an exemplary embodiment of the present specification, the

is any one selected from the following structures.

In the structure,

R31 to R35 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 heteroaryl group, or a substituted or unsubstituted ring may be formed by bonding with an adjacent group.

According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted carbon number by bonding to each other. 3 to 30 monocyclic or polycyclic aliphatic hydrocarbon rings may be formed.

According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted carbon number by bonding to each other. 3 to 20 monocyclic or polycyclic aliphatic hydrocarbon rings may be formed.

According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted carbon number by bonding to each other. 3 to 10 monocyclic or polycyclic aliphatic hydrocarbon rings may be formed.

According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aliphatic hydrocarbon having 3 to 30 carbon atoms in combination with each other. rings can be formed.

According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently a linear or branched alkyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic aliphatic hydrocarbon having 3 to 20 carbon atoms in combination with each other. rings can be formed.

According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently a linear or branched alkyl group having 1 to 10 carbon atoms, or a monocyclic or polycyclic aliphatic hydrocarbon having 3 to 10 carbon atoms in combination with each other. rings can be formed.

According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently a methyl group; ethyl group; Or an isopropyl group, combined with each other to cyclohexane; or cyclopentane.

According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently represents a substituted or unsubstituted C1-C30 linear or branched alkyl group.

According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently represents a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently a linear or branched alkyl group having 1 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently a linear or branched alkyl group having 1 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently a linear or branched alkyl group having 1 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently a methyl group; ethyl group; or an isopropyl group.

According to an exemplary embodiment of the present specification, R1 and R2 may be combined with each other to form a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, R1 and R2 may be combined with each other to form a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, R1 and R2 may be combined with each other to form a substituted or unsubstituted monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, R1 and R2 may be combined with each other to form a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, R1 and R2 may be combined with each other to form a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, R1 and R2 may be combined with each other to form a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, R1 and R2 are combined with each other to form cyclohexane; or cyclopentane.

According to an exemplary embodiment of the present specification, R3 is hydrogen; heavy hydrogen; a substituted or unsubstituted C1-C30 linear or branched alkyl group; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted, monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms including a 6-membered ring including N; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, including O, or S, or a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms by bonding to an adjacent group. ; Alternatively, a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms may be formed.

According to an exemplary embodiment of the present specification, R3 is hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C20 linear or branched alkyl group; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; A substituted or unsubstituted, monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms including a 6-membered ring including N; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms, including O, or S, or a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms by bonding to an adjacent group. ; Alternatively, a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 20 carbon atoms may be formed.

According to an exemplary embodiment of the present specification, R3 is hydrogen; heavy hydrogen; a linear or branched alkyl group having 1 to 30 carbon atoms; A cyano group, a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with a cyano group, or a straight or branched chain alkyl group having 1 to 30 carbon atoms substituted with an alkyl group having 1 to 30 carbon atoms A monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms substituted with a cyano group, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with an aryl group having 2 to 30 carbon atoms a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with a 30 monocyclic or polycyclic heteroaryl group; A monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, including a 6-membered ring including N, which is unsubstituted or substituted with a cyano group or a linear or branched alkyl group having 1 to 30 carbon atoms; Or a cyano group, or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms including O, or S, which is unsubstituted or substituted with a cyano group, or a linear or branched alkyl group having 1 to 30 carbon atoms, or an adjacent group bonded to each other to have carbon atoms 6 to 30 monocyclic or polycyclic aromatic hydrocarbon ring; Or it may form a monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, R3 is hydrogen; heavy hydrogen; a linear or branched alkyl group having 1 to 20 carbon atoms; A cyano group, a linear or branched alkyl group having 1 to 20 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms unsubstituted or substituted with a cyano group, or a straight or branched chain alkyl group having 1 to 20 carbon atoms substituted with an alkyl group A monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms, a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms substituted with a cyano group, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms substituted or unsubstituted with a C2-C20 monocyclic or polycyclic aryl group a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms that is unsubstituted or substituted with a 20 monocyclic or polycyclic heteroaryl group; A monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms, including a 6-membered ring including N, which is unsubstituted or substituted with a cyano group or a linear or branched alkyl group having 1 to 20 carbon atoms; Or a cyano group, or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms, including O, or S, which is unsubstituted or substituted with a cyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms, or an adjacent group bonded to each other to have carbon atoms 6 to 20 monocyclic or polycyclic aromatic hydrocarbon ring; Or it may form a monocyclic or polycyclic heterocycle having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, R3 is hydrogen; heavy hydrogen; methyl group; A cyano group, a pyridine group unsubstituted or substituted with a cyano group, a dibenzofuran group substituted or unsubstituted with a cyano group, a terphenyl group unsubstituted or substituted with a cyano group, a carbazole group, a phenoxazine group, a quinoline group, a triphenylene group , a dibenzothiophene group substituted or unsubstituted with a phenothiazine group, a cyano group, a benzocarbazole group, a phenazine group unsubstituted or substituted with a phenyl group, a fluoranthene group, a dihydroacridine group unsubstituted or substituted with a methyl group, or a phenyl group unsubstituted or substituted with a naphthyl group unsubstituted or substituted with a cyano group; a pyridine group unsubstituted or substituted with a methyl group or a cyano group; phenanthrene group; a naphthyl group unsubstituted or substituted with a cyano group, or a phenyl group unsubstituted or substituted with a cyano group; terphenyl group; quarter phenyl group; a cyano group, or a biphenyl group unsubstituted or substituted with a carbazole group; a dibenzofuran group unsubstituted or substituted with a cyano group; a dibenzothiophene group unsubstituted or substituted with a cyano group; phenalene group; a fluorene group unsubstituted or substituted with a methyl group; triphenylene group; or a fluoranthene group, or benzene by bonding with adjacent groups; or benzofuran.

According to an exemplary embodiment of the present specification, R31 to R35 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C1-C30 linear or branched alkyl group; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted, monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms including a 6-membered ring including N; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, including O, or S, or a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms by bonding to an adjacent group. ; Alternatively, a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms may be formed.

According to an exemplary embodiment of the present specification, R31 to R35 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C20 linear or branched alkyl group; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; A substituted or unsubstituted, monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms including a 6-membered ring including N; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms, including O, or S, or a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms by bonding to an adjacent group. ; Alternatively, a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 20 carbon atoms may be formed.

According to an exemplary embodiment of the present specification, R31 to R35 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a linear or branched alkyl group having 1 to 30 carbon atoms; A cyano group, a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with a cyano group, or a straight or branched chain alkyl group having 1 to 30 carbon atoms substituted with an alkyl group having 1 to 30 carbon atoms A monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms substituted with a cyano group, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with an aryl group having 2 to 30 carbon atoms a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with a 30 monocyclic or polycyclic heteroaryl group; A monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, including a 6-membered ring including N, which is unsubstituted or substituted with a cyano group or a linear or branched alkyl group having 1 to 30 carbon atoms; Or a cyano group, or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms including O, or S, which is unsubstituted or substituted with a cyano group, or a linear or branched alkyl group having 1 to 30 carbon atoms, or an adjacent group bonded to each other to have carbon atoms 6 to 30 monocyclic or polycyclic aromatic hydrocarbon ring; Or it may form a monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, R31 to R35 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a linear or branched alkyl group having 1 to 20 carbon atoms; A cyano group, a linear or branched alkyl group having 1 to 20 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms unsubstituted or substituted with a cyano group, or a straight or branched chain alkyl group having 1 to 20 carbon atoms substituted with an alkyl group A monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms, a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms substituted with a cyano group, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms substituted or unsubstituted with a C2-C20 monocyclic or polycyclic aryl group a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms that is unsubstituted or substituted with a 20 monocyclic or polycyclic heteroaryl group; A monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms, including a 6-membered ring including N, which is unsubstituted or substituted with a cyano group or a linear or branched alkyl group having 1 to 20 carbon atoms; Or a cyano group, or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms, including O, or S, which is unsubstituted or substituted with a cyano group, or a linear or branched alkyl group having 1 to 20 carbon atoms, or an adjacent group bonded to each other to have carbon atoms 6 to 20 monocyclic or polycyclic aromatic hydrocarbon ring; Or it may form a monocyclic or polycyclic heterocycle having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, R31 to R35 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; methyl group; A pyridine group unsubstituted or substituted with a cyano group, a dibenzofuran group, a terphenyl group unsubstituted or substituted with a cyano group, a carbazole group, a phenoxazine group, a quinoline group, a triphenylene group, a phenothiazine group, a dibenzothiophene group, a phenyl group unsubstituted or substituted with a benzocarbazole group, a phenazine group unsubstituted or substituted with a phenyl group, a fluoranthene group, a dihydroacridine group unsubstituted or substituted with a methyl group, or a naphthyl group substituted or unsubstituted with a cyano group; a pyridine group unsubstituted or substituted with a methyl group or a cyano group; phenanthrene group; a naphthyl group unsubstituted or substituted with a phenyl group; terphenyl group; quarter phenyl group; a cyano group, or a biphenyl group unsubstituted or substituted with a carbazole group; dibenzofuran group; dibenzothiophene group; phenalene group; a fluorene group unsubstituted or substituted with a methyl group; triphenylene group; or a fluoranthene group, or benzene by bonding with adjacent groups; benzothiophene; or benzofuran.

According to an exemplary embodiment of the present specification, L1 is a direct bond; a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L1 is a direct bond; a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, L1 is a direct bond; a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L1 is a direct bond; a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms; or a monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, L1 is a direct bond; phenylene group; biphenylrylene group; terphenyl rylene group; naphthylene group; a divalent pyridine group; a divalent furan group; or a divalent thiophene group.

According to an exemplary embodiment of the present specification, L1 is combined with R3 to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present specification, L1 is combined with R3 to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L1 is combined with R3 to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, L1 is combined with R3 to form a ring.

According to an exemplary embodiment of the present specification, L1 is combined with R3 to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L1 is combined with R3 to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, L1 is combined with R3 to form benzene.

According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aliphatic hydrocarbon having 3 to 30 carbon atoms in combination with each other. may form a ring, wherein R3 is hydrogen; heavy hydrogen; a linear or branched alkyl group having 1 to 30 carbon atoms; A cyano group, a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with a cyano group, or a straight or branched chain alkyl group having 1 to 30 carbon atoms substituted with an alkyl group having 1 to 30 carbon atoms A monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms substituted with a cyano group, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with an aryl group having 2 to 30 carbon atoms a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with a 30 monocyclic or polycyclic heteroaryl group; Or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms that is unsubstituted or substituted with a cyano group, or a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic group having 6 to 30 carbon atoms in combination with an adjacent group aromatic hydrocarbon ring; Or it may form a monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms, wherein L1 is a direct bond; a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms.

는 하기 구조 중에서 선택되는 어느 하나이다.According to an exemplary embodiment of the present specification, the

is any one selected from the following structures.

In the above structure, definitions of R31 to R35 are the same as described above.

는 하기 구조 중에서 선택되는 어느 하나이다.According to an exemplary embodiment of the present specification, the

is any one selected from the following structures.

In the structure,

The definition of L1 is the same as defined in Formula 1 above,

11 is an integer of 1 to 4, and when 11 is 2 or more, L1 of 2 or more are the same as or different from each other,

The definitions of R31 to R34 are the same as described above.

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

.

.

The present specification provides an organic light emitting device including the compound represented by Formula 1 above.

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.

In the present specification, the 'layer' means compatible with a 'film' mainly used in the present technical field, and refers to a coating covering a desired area. The size of the 'layers' is not limited, and each of the 'layers' may have the same size or different sizes. According to an exemplary embodiment, the size of the 'layer' may be the same as the entire device, may correspond to the size of a specific functional area, and may be as small as a single sub-pixel.

In the present specification, the meaning that a specific material A is included in layer B means that i) one or more types of material A are included in one layer B, and ii) layer B is composed of one or more layers, and material A is multi-layered B. It includes everything included in one or more floors among the floors.

In the present specification, the meaning that a specific material A is included in the C layer or the D layer means i) is included in one or more of the one or more layers C, ii) is included in one or more of the one or more layers of the D layer, or iii ) means all of which are included in one or more layers C and one or more layers D, respectively.

The present specification includes a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound represented by Formula 1 above. do.

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, it 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, and the like. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.

According to an exemplary embodiment of the present specification, the organic material layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer includes the compound.

According to an exemplary embodiment of the present specification, the organic material layer includes a hole blocking layer, and the hole blocking layer includes the compound.

According to an exemplary embodiment of the present specification, the organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer includes the compound.

According to an exemplary embodiment of the present specification, the organic material layer includes a light emitting layer.

According to an exemplary embodiment of the present specification, the organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer.

According to an exemplary embodiment of the present specification, the organic material layer includes an electron blocking layer.

According to an exemplary embodiment of the present specification, the organic material layer includes a hole blocking layer.

According to an exemplary embodiment of the present specification, the organic light emitting device includes a hole injection layer, a hole transport layer, a hole injection and transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, a hole blocking layer and an electron blocking layer. It further includes one or more floors selected from.

According to an exemplary embodiment of the present specification, the organic light emitting device includes a first electrode; a second electrode provided to face the first 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.

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

According to an exemplary embodiment of the present specification, two or more hole transport layers are included between the light emitting layer and the first electrode. The two or more hole transport layers may include the same or different materials.

According to an exemplary embodiment of the present specification, the first electrode is an anode or a cathode.

According to an exemplary embodiment of the present specification, the second electrode is a cathode or an anode.

According to an 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.

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

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

1 illustrates a structure of an organic light-emitting device in which a first electrode 102 , an organic material layer 111 , and a second electrode 110 are sequentially stacked on a substrate 101 . The compound represented by Formula 1 is included in the organic layer.

2, the first electrode 102, the hole injection layer 103, the hole transport layer 104, the light emitting layer 105, the electron injection and transport layer 106, and the second electrode 110 on the substrate 101 are sequentially The structure of the organic light-emitting device stacked with The compound represented by Formula 1 is included in the electron injection and transport layer.

The organic light emitting device of the present specification includes an electron injection layer, an electron transport layer, an electron injection and transport layer, a hole injection layer, a hole transport layer, a hole injection and transport layer, or a hole blocking layer containing the compound, that is, a compound represented by Formula 1 Except that, it may be prepared by materials and methods known in the art.

When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

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

In addition, the compound represented by Formula 1 may be formed 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, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

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

As the anode material, a material having a large work function is generally preferred so that holes can be smoothly injected into the organic material layer. For example, metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO:Al or SnO ₂ : a combination of a metal such as Sb and an oxide; 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 material is preferably a material having a small work function to facilitate electron injection into the organic material layer. metals or alloys thereof such as, for example, magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead; LiF/Al or a multi-layered material such as LiO ₂ /Al, but is not limited thereto.

The emission layer may include a host material and a dopant material. The host material includes 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, and the like, and heterocyclic-containing compounds include dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives, but is not limited thereto.

According to an exemplary embodiment of the present specification, the host includes a compound represented by the following Chemical Formula H-1, but is not limited thereto.

[Formula H-1]

In Formula H-1,

L20 and L21 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,

Ar20 and Ar21 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,

R201 is hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

r201 is an integer of 1 to 8, and when r201 is 2 or more, 2 or more R201 are the same as or different from each other.

In an exemplary embodiment of the present specification, L20 and L21 are the same as or different from each other, and each independently a direct bond; a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a monocyclic or polycyclic divalent heterocyclic group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, L20 and L21 are the same as or different from each other, and each independently a direct bond; a phenylene group unsubstituted or substituted with deuterium; a biphenylrylene group unsubstituted or substituted with deuterium; a naphthylene group unsubstituted or substituted with deuterium; a divalent dibenzofuran group; or a divalent dibenzothiophene group.

In an exemplary embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic to 4cyclic aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted C 6 to C 20 monocyclic to 4 ring heterocyclic group.

In an exemplary embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently represents a phenyl group unsubstituted or substituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a biphenyl group unsubstituted or substituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthyl group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a thiophene group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a dibenzofuran group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthobenzofuran group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a dibenzothiophene group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a naphthobenzothiophene group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

In an exemplary embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with deuterium; a biphenyl group unsubstituted or substituted with deuterium; terphenyl group; a naphthyl group unsubstituted or substituted with deuterium; a thiophene group unsubstituted or substituted with a phenyl group; phenanthrene group; dibenzofuran group; naphthobenzofuran group; dibenzothiophene group; or a naphthobenzothiophene group.

In an exemplary embodiment of the present specification, Ar20 is a substituted or unsubstituted heterocyclic group, and Ar21 is a substituted or unsubstituted aryl group.

According to an exemplary embodiment of the present specification, R201 is hydrogen.

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

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

According to an exemplary embodiment of the present specification, the dopant includes a compound represented by the following Chemical Formula D-1, but is not limited thereto.

[Formula D-1]

In the formula D-1,

T1 to T6 are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

t5 and t6 are each an integer of 1 to 4,

When t5 is 2 or more, the 2 or more T5 are the same as or different from each other,

When t6 is 2 or more, the 2 or more T6 are the same as or different from each other.

According to an exemplary embodiment of the present specification, T1 to T6 are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted C1-C30 linear or branched alkyl group; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, T1 to T6 are the same as or different from each other, and each independently hydrogen; a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with a cyano group or a linear or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, T1 to T6 are the same as or different from each other, and each independently hydrogen; isopropyl group; a phenyl group substituted with a cyano group; or a phenyl group substituted with a methyl group.

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

The hole injection layer is a layer that receives holes from the electrode. It is preferable that the hole injecting material has the ability to transport holes so as to have a hole receiving effect from the anode and an excellent hole injecting effect for the light emitting layer or the light emitting material. In addition, a material excellent in the ability to prevent movement of excitons generated in the light emitting layer to the electron injection layer or the electron injection material is preferable. In addition, a material excellent in the ability to form a thin film is preferable. In addition, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material, metal porphyrin (porphyrin), oligothiophene, arylamine-based organic material; hexanitrile hexaazatriphenylene-based organic substances; quinacridone-based organic substances; perylene-based organic substances; Polythiophene-based conductive polymers such as anthraquinone and polyaniline, but are not limited thereto.

According to an exemplary embodiment of the present specification, the hole injection layer includes a compound represented by the following Chemical Formula HI-1, but is not limited thereto.

[Formula HI-1]

In the formula HI-1,

R300 to R308 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted ring by combining with an adjacent group,

r301 and r302 are each an integer of 1 to 4,

r303 and r304 are each an integer of 1 to 3,

When r301 is 2 or more, R301 is the same as or different from each other,

When r302 is 2 or more, R302 is the same as or different from each other,

When r303 is 2 or more, R303 is the same as or different from each other,

When r304 is 2 or more, R304 is the same as or different from each other.

According to the temporary state of the present specification, R301 to R304 are hydrogen.

According to the temporary state of the present specification, R300 is a substituted or unsubstituted aryl group.

According to the temporary state of the present specification, R300 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to the temporary state of the present specification, R300 is a phenyl group.

According to an exemplary embodiment of the present specification, R305 to R308 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present specification, R305 to R308 are the same as or different from each other, and each independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms that is unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, R305 to R308 are the same as or different from each other, and each independently a phenyl group; Or a carbazole group unsubstituted or substituted with a phenyl group.

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

The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer. 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 preferable, and a material having high hole mobility is preferable. 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.

According to an exemplary embodiment of the present specification, the hole transport layer includes a compound represented by the following Chemical Formula HT-1, but is not limited thereto.

[Formula HT-1]

In the formula HT-1,

At least one of X'1 to X'6 is N, the rest are CH,

R309 to R314 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted ring by bonding with an adjacent group.

According to an exemplary embodiment of the present specification, X'1 to X'6 are N.

According to an exemplary embodiment of the present specification, R309 to R314 are cyano groups.

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

According to an exemplary embodiment of the present specification, the hole transport layer includes a compound represented by the following Chemical Formula HT-2, but is not limited thereto.

[Formula HT-2]

In the formula HT-2,

R315 to R317 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; a substituted or unsubstituted heteroaryl group; and any one selected from the group consisting of a combination thereof, or a substituted or unsubstituted ring by combining with an adjacent group,

r315 is an integer of 1 to 5, and when r315 is 2 or more, R315 of 2 or more are the same as or different from each other,

r316 is an integer of 1 to 5, and when r316 is 2 or more, 2 or more R316 are the same as or different from each other.

According to an exemplary embodiment of the present specification, R317 is a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; And any one selected from the group consisting of combinations thereof.

According to an exemplary embodiment of the present specification, R317 is a carbazole group; phenyl group; biphenyl group; And any one selected from the group consisting of combinations thereof.

According to an exemplary embodiment of the present specification, R315 and R316 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group, or combine with an adjacent group to form an aromatic hydrocarbon ring substituted with an alkyl group.

According to an exemplary embodiment of the present specification, R315 and R316 are the same as or different from each other, and are each independently a phenyl group, or combine with an adjacent group to form an indene substituted with a methyl group.

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

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. When the organic light emitting device according to an exemplary embodiment of the present specification includes an additional electron transport layer other than the electron transport layer comprising Formula 1, the electron transport material is a material capable of well injecting electrons from the cathode and transferring them to the light emitting layer As such, a material having high electron mobility is preferable. Specific examples include an Al complex of 8-hydroxyquinoline; complexes containing Alq ₃ ; organic radical compounds; hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transport layer may be used with any desired cathode material, as used in accordance with the prior art. In particular, suitable cathode materials are conventional materials having a low work function, followed by a layer of aluminum or silver. Specifically, there are cesium, barium, calcium, ytterbium and samarium, and in each case, an aluminum layer or a silver layer is followed.

The electron injection layer is a layer that receives electrons from the electrode. When the organic light-emitting device according to an exemplary embodiment of the present specification includes an additional electron injection layer other than the electron injection layer comprising Formula 1, the electron injection material has excellent ability to transport electrons, and the second electrode It is preferable to have an electron receiving effect from, and an excellent electron injection effect to the light emitting layer or the light emitting material. In addition, a material that prevents excitons generated in the light emitting layer from moving to the hole injection layer and has excellent thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, preorenylidene methane, anthrone, etc. derivatives thereof; metal complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, and 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. , but is not limited thereto.

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

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 electron injection layer. When the organic light emitting device according to an exemplary embodiment of the present specification includes an additional hole blocking layer other than the hole blocking layer comprising Formula 1, specifically, an oxadiazole derivative or a triazole derivative, a phenanthroline derivative, There is an aluminum complex (aluminum complex), but is not limited thereto.

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

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

Hereinafter, in order to describe the present specification in detail, it will be described in detail with reference to Examples and Comparative Examples. However, the Examples and Comparative Examples according to the present specification may be modified in various other forms, and the scope of the present specification is not to be 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 explain the present specification to those of ordinary skill in the art.

[General formula 1]

An intermediate such as in Preparation Example 2 below can be synthesized by the method of Formula 1 above.

Preparation Example 1

The above compound 1-1a (95.8 g, 296.2 mmol) and dicyanozinc (16.1 g, 137.3 mmol) were added to N,N-dimethylacetamide (1000 mL). After TTP (Tetrakis(triphenylphosphine)palladium, 9.3 g) was added, the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the solid obtained by pouring in water was filtered and recrystallized twice with ethyl acetate to prepare the compound 1-1b. (50.3 g, yield 63%, MS:[M+H]+=270).

Preparation 2

Compound 1-1b (53.2 g, 197.3 mmol) and 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (55.1 g, 217.0 mmol) was added to 1,4-dioxane (600 mL). Potassium acetate (58.0 g) and Pd(dppf)Cl ₂ ([1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), 4.3 g) were added, followed by stirring and refluxing for 12 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare Compound 1-1. (59.9 g, yield 84%, MS:[M+H]+=362).

Synthesis Example 1

The compound 1-1 (10.8 g, 30 mmol) and the compound 1-2 (16.3 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare Compound 1. (13.3 g, yield 82%, MS:[M+H]+= 544).

Synthesis Example 2

The compound 2-1 (15.0 g, 30 mmol) and the compound 2-2 (17.8 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare Compound 2. (11.6 g, yield 65%, MS:[M+H]+=594).

Synthesis Example 3

The compound 3-1 (15.0 g, 30 mmol) and the compound 3-2 (17.8 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare compound 3 above. (13.7 g, yield 77%, MS:[M+H]+=593).

Synthesis Example 4

The compound 4-1 (15.0 g, 30 mmol) and the compound 4-2 (15.5 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare compound 4 above. (13.1 g, yield 85%, MS:[M+H]+=517).

Synthesis Example 5

The compound 5-1 (15.0 g, 30 mmol) and the compound 5-2 (20.0 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare Compound 5. (16.8 g, yield 84%, MS:[M+H]+=667).

Synthesis Example 6

The compound 6-1 (15.0 g, 30 mmol) and the compound 6-2 (14.0 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare Compound 6. (11.9 g, yield 85%, MS:[M+H]+=467).

Synthesis Example 7

The compound 3-1 (15.0 g, 30 mmol) and the compound 7-2 (18.6 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare Compound 7. (16.3 g, yield 88%, MS:[M+H]+=620).

Synthesis Example 8

The compound 7-1 (15.0 g, 30 mmol) and the compound 8-2 (19.0 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare Compound 8. (16.7 g, yield 88%, MS:[M+H]+=634).

Synthesis Example 9

The compound 7-1 (15.0 g, 30 mmol) and the compound 9-2 (17.2 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare compound 9. (13.5 g, yield 79%, MS:[M+H]+=573).

Synthesis Example 10

The compound 8-1 (15.0 g, 30 mmol) and the compound 10-2 (17.0 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare Compound 10. (12.7 g, yield 75%, MS:[M+H]+=567).

Synthesis Example 11

The compound 1-1 (15.0 g, 30 mmol) and the compound 11-2 (17.1 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare Compound 11. (13.8 g, yield 81%, MS:[M+H]+=570).

Synthesis Example 12

The compound 9-1 (15.0 g, 30 mmol) and the compound 12-2 (18.4 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare Compound 12. (13.2 g, yield 72%, MS: [M+H] + = 613).

Synthesis Example 13

The compound 10-1 (15.0 g, 30 mmol) and the compound 13-2 (16.7 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare compound 13. (13.5 g, yield 81 %, MS: [M+H] + = 558).

Synthesis Example 14

The compound 11-1 (15.0 g, 30 mmol) and the compound 14-2 (19.8 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare compound 14. (15.8 g, yield 80%, MS:[M+H]+=660).

Synthesis Example 15

The compound 5-1 (15.0 g, 30 mmol) and the compound 15-2 (15.5 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare compound 15. (12.4 g, yield 80 %, MS: [M+H] + = 517).

Synthesis Example 16

The compound 5-1 (15.0 g, 30 mmol) and the compound 16-2 (13.6 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare compound 16. (9.8 g, yield 72%, MS:[M+H]+=456).

Synthesis Example 17

The compound 3-1 (15.0 g, 30 mmol) and the compound 17-2 (18.9 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare compound 17. (14.2 g, yield 75%, MS:[M+H]+=632).

Synthesis Example 18

The compound 12-1 (15.0 g, 30 mmol) and the compound 18-2 (19.8 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare compound 18. (15.2 g, yield 77%, MS:[M+H]+=660).

Synthesis Example 19

The compound 13-1 (15.0 g, 30 mmol) and the compound 19-2 (16.0 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare Compound 19. (14.4 g, yield 90 %, MS: [M+H] + = 536).

Synthesis Example 20

The compound 11-1 (15.0 g, 30 mmol) and the compound 20-2 (20.8 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare Compound 20. (17.1 g, yield 82 %, MS: [M+H] + = 696).

Synthesis Example 21

The compound 5-1 (15.0 g, 30 mmol) and the compound 21-2 (15.9 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare Compound 21. (13.2 g, yield 83%, MS:[M+H]+=532).

Synthesis Example 22

The compound 3-1 (15.0 g, 30 mmol) and the compound 22-2 (16.2 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare Compound 22. (12.1 g, yield 75%, MS:[M+H]+=541).

Synthesis Example 23

The compound 2-1 (15.0 g, 30 mmol) and the compound 23-2 (17.0 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare the compound 23. (10.4 g, yield 61%, MS:[M+H]+=569).

Synthesis Example 24

The compound 14-1 (15.0 g, 30 mmol) and the compound 24-2 (19.0 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare Compound 24. (15.4 g, yield 81 %, MS: [M+H] + = 636).

Synthesis Example 25

The compound 15-1 (15.0 g, 30 mmol) and the compound 25-2 (16.0 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare the compound 25. (12.6 g, yield 79%, MS:[M+H]+=533).

Synthesis Example 26

The compound 26-1 (15.0 g, 30 mmol) and the compound 26-2 (8.8 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare the compound 26. (9.8 g, yield 70%, MS:[M+H]+=467).

Synthesis Example 27

The compound 26-1 (15.0 g, 30 mmol) and the compound 27-2 (12.8 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare compound 27. (13.0 g, yield 80%, MS:[M+H]+=543).

Synthesis Example 28

The compound 26-1 (15.0 g, 30 mmol) and the compound 28-2 (15.3 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare Compound 28. (14.3 g, yield 77%, MS:[M+H]+=619).

Synthesis Example 29

The compound 26-1 (15.0 g, 30 mmol) and the compound 29-2 (12.8 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K ₂ CO ₃ (200 mL), potassium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligands were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid by filtration was recrystallized twice with ethyl acetate to prepare the compound 29. (12.9 g, yield 79 %, MS: [M+H] + = 543).

Example 1

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

On the thus prepared ITO transparent electrode, the following compound [HI-A] was thermally vacuum-deposited to a thickness of 600 Å to form a hole injection layer. On the hole injection layer, 50 Å of hexanitrile hexaazatriphenylene (HAT) of the following formula and the following compound [HT-A] (600 Å) were sequentially vacuum-deposited to form a hole transport layer.

Then, the following compounds [BH] and [BD] were vacuum-deposited in a weight ratio of 25:1 to a thickness of 200 Å on the hole transport layer to form a light emitting layer. On the light emitting layer, the compound 1 and [LiQ] (Lithiumquinolate) were vacuum-deposited in a 1:1 weight ratio to form an electron injection and transport layer to a thickness of 350 Å. A cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 10 Å and aluminum to a thickness of 1,000 Å on the electron injection and transport layer.

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

Example 2

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 2 was used instead of Compound 1 of the electron injection and transport layer in Example 1.

Example 3

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 3 was used instead of Compound 1 in the electron injection and transport layer in Example 1.

Example 4

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 4 was used instead of Compound 1 of the electron injection and transport layer in Example 1.

Example 5

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 5 was used instead of Compound 1 of the electron injection and transport layer in Example 1.

Example 6

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 6 was used instead of Compound 1 in the electron injection and transport layer in Example 1.

Example 7

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 7 was used instead of Compound 1 in the electron injection and transport layer in Example 1.

Example 8

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 8 was used instead of Compound 1 of the electron injection and transport layer in Example 1.

Example 9

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 9 was used instead of Compound 1 as the electron injection and transport layer in Example 1.

Example 10

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 10 was used instead of Compound 1 of the electron injection and transport layer in Example 1.

Example 11

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 11 was used instead of Compound 1 of the electron injection and transport layer in Example 1.

Example 12

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 12 was used instead of Compound 1 of the electron injection and transport layer in Example 1.

Example 13

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 13 was used instead of Compound 1 in the electron injection and transport layer in Example 1.

Example 14

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 14 was used instead of Compound 1 of the electron injection and transport layer in Example 1.

Example 15

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 15 was used instead of Compound 1 of the electron injection and transport layer in Example 1.

Example 16

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 16 was used instead of Compound 1 of the electron injection and transport layer in Example 1.

Example 17

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 17 was used instead of Compound 1 in the electron injection and transport layer in Example 1.

Example 18

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 18 was used instead of Compound 1 of the electron injection and transport layer in Example 1.

Example 19

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 19 was used instead of Compound 1 in the electron injection and transport layer in Example 1.

Example 20

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 20 was used instead of Compound 1 of the electron injection and transport layer in Example 1.

Example 21

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 21 was used instead of Compound 1 of the electron injection and transport layer in Example 1.

Example 22

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 22 was used instead of Compound 1 in the electron injection and transport layer in Example 1.

Example 23

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 23 was used instead of Compound 1 in the electron injection and transport layer in Example 1.

Example 24

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 24 was used instead of Compound 1 of the electron injection and transport layer in Example 1.

Example 25

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 25 was used instead of Compound 1 of the electron injection and transport layer in Example 1.

Example 26

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 26 was used instead of Compound 1 of the electron injection and transport layer in Example 1.

Example 27

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 27 was used instead of Compound 1 of the electron injection and transport layer in Example 1.

Example 28

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 28 was used instead of Compound 1 of the electron injection and transport layer in Example 1.

Example 29

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 29 was used instead of Compound 1 of the electron injection and transport layer in Example 1.

Comparative Example 1

An organic light emitting diode was manufactured in the same manner as in Example 1, except that the following compound ET1 was used instead of Compound 1 in the electron injection and transport layer in Example 1.

[ET1]

Comparative Example 2

An organic light emitting diode was manufactured in the same manner as in Example 1, except that the following compound ET2 was used instead of Compound 1 in the electron injection and transport layer in Example 1.

[ET2]

Comparative Example 3

An organic light emitting diode was manufactured in the same manner as in Example 1, except that the following compound ET3 was used instead of Compound 1 in the electron injection and transport layer in Example 1.

[ET3]

Comparative Example 4

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound ET4 below was used instead of Compound 1 in the electron injection and transport layer in Example 1.

[ET4]

Comparative Example 5

An organic light emitting diode was manufactured in the same manner as in Example 1, except that the following compound ET5 was used instead of Compound 1 in the electron injection and transport layer in Example 1.

[ET5]

Comparative Example 6

An organic light emitting diode was manufactured in the same manner as in Example 1, except that the following compound ET6 was used instead of Compound 1 in the electron injection and transport layer in Example 1.

[ET6]

Comparative Example 7

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound ET7 below was used instead of Compound 1 in the electron injection and transport layer in Example 1.

[ET7]

As in Examples 1 to 29 and Comparative Examples 1 to 7, the organic light emitting device manufactured by using each compound as an electron injection and transport layer material was measured for driving voltage and luminous efficiency at a current density of 10 mA/cm ² , At a current density of 20 mA/cm ² , the time (LT98) to be 98% of the initial luminance was measured.

The results are shown in Table 1 below.

division compound Voltage
(V) current efficiency
(cd/A) Life Time 98 at 20mA/cm ² Example 1 compound 1 3.48 5.51 80 Example 2 compound 2 3.62 5.50 95 Example 3 compound 3 3.71 5.32 70 Example 4 compound 4 3.75 5.22 70 Example 5 compound 5 3.63 5.21 80 Example 6 compound 6 3.83 5.50 95 Example 7 compound 7 3.52 5.24 75 Example 8 compound 8 3.75 5.15 70 Example 9 compound 9 3.81 5.12 80 Example 10 compound 10 3.83 5.15 80 Example 11 compound 11 3.91 5.21 70 Example 12 compound 12 4.01 5.22 65 Example 13 compound 13 3.53 5.35 80 Example 14 compound 14 3.78 5.20 75 Example 15 compound 15 3.88 5.26 70 Example 16 compound 16 3.69 5.40 75 Example 17 compound 17 3.78 5.49 75 Example 18 compound 18 3.77 5.50 70 Example 19 compound 19 3.70 5.51 65 Example 20 compound 20 3.81 5.20 90 Example 21 compound 21 3.88 5.13 80 Example 22 compound 22 3.78 5.15 70 Example 23 compound 23 3.79 5.12 70 Example 24 compound 24 3.88 5.30 80 Example 25 compound 25 3.90 5.20 70 Example 26 compound 26 3.83 5.12 90 Example 27 compound 27 3.60 5.48 60 Example 28 compound 28 3.67 5.15 85 Example 29 compound 29 3.70 5.21 70 Comparative Example 1 ET1 4.35 4.52 35 Comparative Example 2 ET2 5.00 3.50 45 Comparative Example 3 ET3 5.11 3.70 30 Comparative Example 4 ET4 5.10 3.20 50 Comparative Example 5 ET5 5.05 3.15 50 Comparative Example 6 ET6 4.40 4.55 30 Comparative Example 7 ET7 4.52 4.60 20

As the result of Table 1, the N-containing heterocyclic group derivative of Formula 1 and the cyano group have an electron depletion structure, so that the dipole moment of the molecule can be increased. The electron mobility of the light emitting device is smoothly controlled. Therefore, it was confirmed that the driving voltage, current efficiency, and lifespan of the organic light emitting diodes of Examples 1 to 29 exhibited superior characteristics than the compounds of Comparative Examples 1 to 7. In addition, the polarity of the molecule is higher in Example 21 of the present application, in which R3 includes a compound containing a 6-membered ring including N, than Comparative Example 5, in which R3 includes a compound containing a benzimidazole (5-membered ring including N), Since electron migration can be controlled relatively smoothly by the resonance structure, it can be seen that the driving voltage, current efficiency, and lifespan are excellent. Formula 1 represents xanthene (or thioxanthene), a cyano group, and an N-containing monocyclic heterocyclic ring The groups are organically bonded to each other, and Comparative Examples 6 and 7 are organic light emitting devices including a compound including a spirobifluorene (fluorene) structure instead of xanthene (or thioxanthene), It was found that Examples 1 to 29, which are organic light emitting devices represented by Chemical Formula 1, had better driving voltage, current efficiency, and lifespan than Comparative Examples 6 and 7.

101: substrate
102: first electrode
111: organic layer
110: second electrode
103: hole injection layer
104: hole transport layer
105: light emitting layer
106: electron injection and transport layer

Claims (10)

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

In Formula 1,
X1 is O or S;
At least one of Y1 to Y5 is N, and the others are each independently CR3,
R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group, may be combined with each other to form a substituted or unsubstituted aliphatic hydrocarbon ring,
R3 is hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group including a 6-membered ring including N; Or a substituted or unsubstituted, O, or a heteroaryl group containing S, or may combine with an adjacent group to form a substituted or unsubstituted ring,
L1 is a direct bond; a substituted or unsubstituted alkylene group; a substituted or unsubstituted alkenylene group; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
l1 is an integer from 1 to 5,
m is 1 or 2,
n is an integer from 1 to 4,
When l1 is 2 or more, the 2 or more L1s are the same as or different from each other,
When n is 2 or more, the 2 or more

are the same as or different from each other,

denotes a site at which L1 is bonded to Formula 1. The method according to claim 1, wherein Chemical Formula 1 is a compound represented by the following Chemical Formula 2 or 3:
[Formula 2]

[Formula 3]

In Formulas 2 and 3,
R1, R2, Y1 to Y5, L1, 11, m, and n are the same as defined in Formula 1 above. The method according to claim 1, wherein Chemical Formula 1 is a compound represented by the following Chemical Formula 4 or 5:
[Formula 4]

[Formula 5]

In Formulas 4 and 5,
X1, R1, R2, Y1 to Y5, L1 and 11 are the same as defined in Formula 1 above. The compound according to claim 1, wherein Formula 1 is represented by any one of Formulas 6 to 9:
[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

In Formulas 6 to 9,
R1, R2, Y1 to Y5, L1 and 11 are the same as defined in Formula 1 above. The method according to claim 1, wherein R1 and R2 are the same as or different from each other, and each independently a linear or branched alkyl group having 1 to 30 carbon atoms, or combined with each other to form a monocyclic or polycyclic aliphatic hydrocarbon ring having 3 to 30 carbon atoms. can,
wherein R3 is hydrogen; heavy hydrogen; a linear or branched alkyl group having 1 to 30 carbon atoms; A cyano group, a linear or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with a cyano group, or a straight or branched chain alkyl group having 1 to 30 carbon atoms is substituted with a cyano group. A monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms substituted with a cyano group, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with an aryl group having 2 to 30 carbon atoms a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms unsubstituted or substituted with a 30 monocyclic or polycyclic heteroaryl group; A monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, including a 6-membered ring including N, which is unsubstituted or substituted with a cyano group or a linear or branched alkyl group having 1 to 30 carbon atoms; Or a cyano group, or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms including O, or S, which is unsubstituted or substituted with a cyano group, or a linear or branched alkyl group having 1 to 30 carbon atoms, or an adjacent group bonded to each other to have carbon atoms 6 to 30 monocyclic or polycyclic aromatic hydrocarbon ring; Or it may form a monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms,
L1 is a direct bond; a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; Or a compound that is a monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms. The compound according to claim 1, wherein Formula 1 is any one selected from the following compounds:

. a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises the compound of any one of claims 1 to 6. The organic light-emitting device of claim 7 , wherein 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 organic light emitting diode of claim 7 , wherein the organic material layer includes a hole blocking layer, and the hole blocking layer includes the compound. The organic light-emitting device of claim 7 , wherein 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 includes the compound.

Images