KR102117765B1 - Multicyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification provides a compound of Formula 1 and an organic light emitting device including the same.

Description

A polycyclic compound and an organic light emitting device comprising the same{MULTICYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME}

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

The organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from the two electrodes are combined in an organic thin film to form a pair, and then disappear and shine. The organic thin film may be composed of a single layer or multiple layers if necessary.

In general, the organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode and a cathode and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic light emitting device, the organic material layer is often composed of a multi-layered structure composed of different materials, for example, may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. When a voltage is applied between two electrodes in the structure of the organic light emitting device, holes are injected at the anode, and electrons are injected at the cathode, and an exciton is formed when the injected holes meet the electrons. When it falls to the ground again, it glows.

The development of new materials for such organic light emitting devices continues to be required.

Korean Patent Publication No. 2000-0051826

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

One embodiment of the present specification provides a compound represented by the following Chemical Formula 1.

[Formula 1]

In Chemical Formula 1,

A1 and A2 are the same as or different from each other, and each independently an substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocycle,

X, Y, Z and W are the same or different from each other, each independently O, S, NRa or CRbRc,

Ra, Rb and Rc are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R ₁ to R ₁₂ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted ring.

In addition, according to an exemplary embodiment of the present specification, the first electrode; A second electrode provided opposite to the first electrode; And an organic light emitting device including at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the above-described compound.

The compounds described herein can be used as a material for the organic material layer of the organic light emitting device. The compound according to at least one exemplary embodiment is capable of high-intensity light emission in an organic light emitting device, and can improve efficiency, improve low driving voltage, and/or lifespan characteristics. In particular, the compounds described herein can be used as hole injection, hole transport, hole injection and hole transport, electron suppression, luminescence, hole suppression, electron transport, or electron injection materials.

1 shows an example of an organic light emitting device including a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
FIG. 2 shows an example of an organic light emitting device comprising a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8, and a cathode 4 Did.

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

The present specification provides a compound represented by Formula 1 below. The compound represented by Chemical Formula 1 contains boron (B) and has a core structure of a polygonal ring, and thus has a very hard structure, and thus has a very small Stokes shift, and thus may exhibit a narrow half width. With this function, it is possible to implement an organic light emitting device having a high color gamut. In addition, when the compound of the present application is used in the light emitting layer according to an example, it is possible to realize an organic light emitting device having a long life and high efficiency by minimizing the mutual interaction with respect to excitons generated in the light emitting layer.

[Formula 1]

In Chemical Formula 1,

A1 and A2 are the same as or different from each other, and each independently an substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocycle,

X, Y, Z and W are the same as or different from each other, and each independently O, S, NRa or CRbRc,

Ra, Rb and Rc are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R ₁ to R ₁₂ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted ring.

는 다른 치환기 또는 결합부에 결합되는 부위를 의미한다.In this specification,

Means a site that is attached to another substituent or linkage.

In the present specification, when a part is to “include” a certain component, it means that the component may further include other components, not to exclude other components, unless otherwise stated.

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

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

The term "substitution" means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is substituted, that is, a position where the substituent is substitutable, and when two or more are substituted , 2 or more substituents may be the same or different from each other.

The term "substituted or unsubstituted" as used herein refers to deuterium; Halogen group; Nitrile group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; And substituted or unsubstituted heterocyclic groups, substituted with 1 or 2 or more substituents selected from the group, or substituted with 2 or more substituents among the exemplified substituents, or having no substituents. For example, "a substituent having two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are connected.

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

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

In the present specification, the silyl group may be represented by the formula of -SiA _a A _b A _c , wherein A _a , A _b and A _c are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The silyl group is specifically trimethylsilyl group (TMS), triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. It is not limited to this.

In the present specification, the boron group may be represented by the formula of -BA _a A _b , wherein A _a and A _b are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The boron group is specifically a trimethyl boron group, a triethyl boron group, a t-butyl dimethyl boron group, a triphenyl boron group, a phenyl boron group, and the like, but is not limited thereto.

In the present specification, the alkyl group may be straight chain or branched chain, and carbon number is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group are methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, pentyl group, n-pentyl group , Isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, heptyl group, n-heptyl group, octyl group, n-octyl group, tert-octyl group and the like, but is not limited to these. Does not.

In the present specification, the alkoxy group may be a straight chain, branched chain or cyclic chain. The number of carbon atoms of the alkoxy group is not particularly limited, and is 1 to 40 carbon atoms, and according to an embodiment, 1 to 20 carbon atoms. Specifically, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, tert-butoxy group, sec-butoxy group, n-pentyloxy group, neopentyloxy group, isopentyloxy group , n-hexyloxy group, n-octyloxy group, n-nonyloxy group, n-decyloxy group, benzyloxy group, p-methylbenzyloxy group, and the like, but is not limited thereto.

Substituents comprising alkyl, alkoxy, and other alkyl group moieties described herein include both straight-chain or ground forms.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 40 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, a cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, and the like, but is not limited thereto.

In the present specification, the amine group is -NH ₂ ; Alkylamine groups; N-aryl alkylamine group; Arylamine group; N-aryl heteroarylamine group; It may be selected from the group consisting of N-alkylheteroarylamine groups and heteroarylamine groups, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30.

In the present specification, the number of carbon atoms in the alkylamine group is not particularly limited, but is preferably 1 to 40. Specific examples of the alkylamine group include a methylamine group, a dimethylamine group, an ethylamine group, and a diethylamine group, but are not limited thereto.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group including the 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.

Specific examples of the arylamine group include, but are not limited to, phenylamine, naphthylamine, biphenylamine, anthracenylamine, diphenyl amine group, phenyl naphthyl amine group, and the like.

In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group. The heteroaryl group in the heteroarylamine group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group. The heteroarylamine group including two or more heterocyclic groups may include a monocyclic heterocyclic group, a polycyclic heterocyclic group, or a monocyclic heterocyclic group and a polycyclic heterocyclic group simultaneously.

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

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

,

등의 스피로플루오레닐기,

(9,9-디메틸플루오레닐기), 및

(9,9-디페닐플루오레닐기) 등의 치환된 플루오레닐기가 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

Spirofluorenyl groups such as,

(9,9-dimethylfluorenyl group), and

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

In the present specification, a heterocyclic group is a heteroatom as a heterocyclic group containing one or more of N, O, P, S, Si, and Se, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. According to one embodiment, the heterocyclic group has 2 to 30 carbon atoms. Examples of the heterocyclic group include pyridyl group, pyrrol group, pyrimidyl group, pyridazinyl group, furanyl group, thiophenyl group, imidazole group, pyrazole group, oxazole group, isooxazole group, thiazole group, carbazole group, di Benzofuranyl groups, dibenzothiophenyl groups, and the like, but are not limited to these.

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

In this specification, "adjacent" A group may refer to a substituent substituted on an atom directly connected to an atom in which the substituent is substituted, a substituent positioned closest to the substituent and the other substituent substituted in the atom to which the substituent is substituted. For example, two substituents substituted at the ortho position on the benzene ring and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" to each other.

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

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

In this specification, the description of the aryl group can be applied, except that the aromatic hydrocarbon ring is divalent.

In the present specification, the heterocycle is a non-carbon atom, and contains at least one heteroatom, specifically, the heteroatom contains at least one atom selected from the group consisting of N, O, P, S, Si and Se, etc. can do. The heterocyclic ring may be monocyclic or polycyclic, aromatic, aliphatic or aromatic and aliphatic condensed ring, and may be selected from examples of the heteroaryl group except that it is a divalent group.

In one embodiment of the present specification, R ₁ to R ₁₂ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Silyl group; Boron group; A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

According to another exemplary embodiment, R ₁ to R ₁₂ 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 amine group; Or a substituted or unsubstituted heterocyclic group.

In another exemplary embodiment, R ₁ to R ₁₂ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted arylamine group having 12 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

According to another exemplary embodiment, R ₁ to R ₁₂ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted arylamine group having 12 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In another exemplary embodiment, R ₁ to R ₁₂ are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted arylamine group.

According to another exemplary embodiment, R ₁ to R ₁₂ are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted arylamine group having 12 to 60 carbon atoms.

According to another exemplary embodiment, R ₁ to R ₁₂ are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted diphenylamine group.

In one embodiment of the present specification, A1 and A2 are the same as or different from each other, and each independently a substituted or unsubstituted benzene ring.

According to another exemplary embodiment, A1 and A2 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amine group, and a substituted or unsubstituted A substituted or unsubstituted benzene ring selected from the group consisting of heterocyclic groups.

 In another exemplary embodiment, A1 and A2 are the same as or different from each other, and each independently substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or It is a substituted or unsubstituted benzene ring selected from the group consisting of an unsubstituted arylamine group having 12 to 30 carbon atoms and a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

로 이루어진 군으로부터 선택된 1 이상으로 치환 또는 비치환된 벤젠고리이다.According to another exemplary embodiment, A1 and A2 are the same as or different from each other, and each independently a methyl group, ethyl group, propyl group, isopropyl group, butyl group, tert-butyl group, phenyl group, biphenyl group, naphthyl group, Diphenylamine group, diphenylamine group substituted with tert-butyl group, carbazole group, carbazole group substituted with tert-butyl group, phenoxazinyl group (phenoxazine), and

It is a substituted or unsubstituted benzene ring selected from the group consisting of.

According to an exemplary embodiment of the present specification, the formula 1 may be represented by the following formula (2).

[Formula 2]

In Chemical Formula 2,

X, Y, Z and W are the same as defined in Formula 1,

R ₂₁ to R ₂₆ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

n1 to n6 are each an integer of 0 to 3, and when n1 to n6 are each 2 or more, the substituents in parentheses are the same or different from each other.

In one embodiment of the present specification, R ₂₁ , R ₂₃ , R ₂₄ , and R ₂₆ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Silyl group; Boron group; A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

According to another exemplary embodiment, R ₂₁ , R ₂₃ , R ₂₄ , and R ₂₆ 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 amine group; Or a substituted or unsubstituted heterocyclic group.

In another exemplary embodiment, R ₂₁ , R ₂₃ , R ₂₄ , and R ₂₆ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted arylamine group having 12 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

According to another exemplary embodiment, R ₂₁ , R ₂₃ , R ₂₄ , and R ₂₆ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted arylamine group having 12 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In another exemplary embodiment, R ₂₁ , R ₂₃ , R ₂₄ , and R ₂₆ are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted arylamine group.

According to another exemplary embodiment, R ₂₁ , R ₂₃ , R ₂₄ , and R ₂₆ are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted arylamine group having 12 to 60 carbon atoms.

According to another exemplary embodiment, R ₂₁ , R ₂₃ , R ₂₄ , and R ₂₆ are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted diphenylamine group.

According to the exemplary embodiment of the present specification, R ₂₂ and R ₂₅ 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; A substituted or unsubstituted amine group; Or a substituted or unsubstituted heterocyclic group.

According to another exemplary embodiment, R ₂₂ and R ₂₅ are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted arylamine group having 12 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

이다.In another exemplary embodiment, R ₂₂ and R ₂₅ are the same as or different from each other, and each independently hydrogen; Methyl group, ethyl group, propyl group, isopropyl group, butyl group, tert-butyl group, phenyl group, biphenyl group, naphthyl group, diphenylamine group, diphenylamine group substituted with tert-butyl group, carbazole group, tert-butyl group Substituted carbazole group, phenoxazinyl group (phenoxazine) or

to be.

According to an exemplary embodiment of the present specification, each of n1 to n6 is 0 or 1.

According to one embodiment of the present specification, X, Y, Z, and W are the same as or different from each other, and each independently O, S, NRa, or CRbRc.

According to an exemplary embodiment of the present specification, the X, Y, Z and W are NRa.

According to another exemplary embodiment, X, Y, Z and W are O.

In another exemplary embodiment, X, Y, Z and W are S.

According to another exemplary embodiment, two of the X, Y, Z and W are NRa, and two are O.

In another exemplary embodiment, two of X, Y, Z, and W are NRa, and two are CRbRc.

According to another exemplary embodiment, three of the X, Y, Z, and W are NRa, and one is O.

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

According to another exemplary embodiment, Rb and Rc are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

In another exemplary embodiment, Rb and Rc are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to another exemplary embodiment, Rb and Rc are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted n-propyl group; A substituted or unsubstituted isopropyl group; A substituted or unsubstituted n-butyl group; A substituted or unsubstituted tert-butyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; Or a substituted or unsubstituted naphthyl group.

In another exemplary embodiment, Rb and Rc are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Methyl group; Ethyl group; n-propyl group; Isopropyl group; n-butyl group; tert-butyl group; Phenyl group; Biphenyl group; Terphenyl group; Or a naphthyl group.

According to another exemplary embodiment, Rb and Rc are methyl groups.

According to an exemplary embodiment of the present specification, Ra is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

According to another exemplary embodiment, Ra is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; A substituted or unsubstituted arylamine group having 12 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

In another exemplary embodiment, Ra is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

According to another exemplary embodiment, Ra is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In another exemplary embodiment, Ra is hydrogen; An alkyl group having 1 to 20 carbon atoms; Or an aryl group unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms.

According to another exemplary embodiment, Ra is hydrogen; Methyl group; Ethyl group; Propyl group; Isopropyl group; Butyl group; tert-butyl group; A phenyl group unsubstituted or substituted with a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group or a tert-butyl group; tert-butyl group; A biphenyl group unsubstituted or substituted with a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group or a tert-butyl group; Or tert-butyl group; It is a naphthyl group unsubstituted or substituted with a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group or a tert-butyl group.

In another exemplary embodiment, Ra is a phenyl group substituted with an ethyl group, a phenyl group, or a tert-butyl group.

According to an exemplary embodiment of the present specification, the compound represented by Formula 1 may be selected from the following compounds.

Compound 1 Compound 2 Compound 3

Compound 4 Compound 5 Compound 6

Compound 7 Compound 8 Compound 9

Compound 10 Compound 11 Compound 12

Compound 13 Compound 14 Compound 15

Compound 16 Compound 17 Compound 18

Compound 19 Compound 20 Compound 21

Compound 22 Compound 23

The compound of Formula 1 according to an exemplary embodiment of the present specification may be prepared by the following manufacturing method.

<General Manufacturing Method of Formula 1>

[A1] [A2] [A3] [A4]

A3 can be synthesized using starting materials A1 and A2 and a palladium catalyst or base. (Ha means a halogen element such as Br, Cl, F, and is the same below.) A4 can be synthesized by removing the carbonyl group from A3 using iodine and hypophosphorous acid.

[A1] [B1] [B2]

B2 can be synthesized through a catalyst or base coupling reaction between the starting materials A1 and B1.

[A4] [B2] [C1] [C2]

Intermediates C1 can be obtained by forming spiro rings under the basic conditions using the intermediates A4 and B2, respectively, and the target C2 can be synthesized after boron tribromide treatment under the basic conditions.

The spiro ring can be formed by other methods even if it is not necessarily such a condition. In addition, when various types of substituents are used for A1, A2, and B1, compounds having various structures included in Chemical Formula 1 may be formed.

For example, the compound of Formula 1 may have a core structure as in a manufacturing method described later. Substituents can be combined by methods known in the art, and the type, location, or number of substituents can be varied according to techniques known in the art.

The conjugation length of the compound and the energy band gap are closely related. Specifically, the longer the conjugation length of the compound, the smaller the energy band gap.

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

In addition, by introducing various substituents to the core structure of the structure as described above, it is possible to synthesize a compound having intrinsic properties of the introduced substituents. For example, by introducing a substituent mainly used for a hole injection layer material, a hole transport material, a light emitting layer material, and an electron transport layer material used in manufacturing an organic light emitting device into the core structure, a material satisfying the conditions required for each organic material layer can be synthesized. Can be.

In addition, the organic light emitting device according to the present invention includes a first electrode; A second electrode provided opposite to the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the compound of Formula 1.

The organic light-emitting device of the present invention can be manufactured by a conventional manufacturing method and material of an organic light-emitting device, except that one or more organic material layers are formed using the above-described compound.

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

The organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention 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, etc. as an organic material layer. However, the structure of the organic light emitting device is not limited thereto, and may include a smaller number of organic material layers.

In the organic light emitting device of the present invention, the organic material layer may include an electron transport layer or an electron injection layer, and the electron transport layer or electron injection layer may include a compound represented by Chemical Formula 1.

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

In another exemplary embodiment, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1.

According to another exemplary embodiment, the organic material layer includes a light emitting layer, and the light emitting layer may include a compound represented by Chemical Formula 1 as a dopant in the light emitting layer.

In another exemplary embodiment, the organic material layer including the compound represented by Chemical Formula 1 includes the compound represented by Chemical Formula 1 as a dopant, includes a fluorescent host or a phosphorescent host, and other organic compounds, metals or metal compounds It may include as a dopant.

According to another exemplary embodiment, the organic material layer including the compound represented by Chemical Formula 1 may include a compound represented by Chemical Formula 1 as a dopant, and may include a fluorescent host or a phosphorescent host. The dopant may include 0.01 to 20 parts by weight based on 100 parts by weight of the host.

As another example, the organic material layer including the compound represented by Chemical Formula 1 includes the compound represented by Chemical Formula 1 as a dopant, includes a fluorescent host or a phosphorescent host, and can be used with an iridium-based (Ir) dopant. have.

According to a specific example, the organic material layer including the compound represented by Chemical Formula 1 may include a compound represented by Chemical Formula 1 as a dopant, and further include a host compound represented by Chemical Formula A or B below.

[Formula A]

[Formula B]

In Formulas A and B, R101 to R105 are each independently an aryl group or a heteroaryl group, and these substituents may be further substituted with an aryl group or heteroaryl group.

According to an example, the R101 to R105 are the same as or different from each other, and may be a phenyl group, a naphthyl group, a naphthyl group substituted with phenyl, a phenyl group substituted with a naphthyl group, a dibenzofuran group, or a dibenzothiophene group.

According to another example, in Chemical Formula A, R101 and R102 are aryl groups.

According to another example, in the formula (A), R101 and R102 are the same as or different from each other, and are a phenyl group, a naphthyl group, a naphthyl group substituted with phenyl, or a phenyl group substituted with a naphthyl group.

According to another example, in Chemical Formula A, R101 is an aryl group and R102 is a heteroaryl group.

According to another example, in Chemical Formula A, R101 is a phenyl group, a naphthyl group, a naphthyl group substituted with phenyl, or a phenyl group substituted with a naphthyl group, and R102 may be a dibenzofuran group or a dibenzothiophene group. .

According to another example, in Chemical Formula B, R105 is an aryl group, and R103 and R104 are the same or different from each other and are heteroaryl groups.

According to another example, in Chemical Formula B, R105 is a phenyl group, a naphthyl group, a naphthyl group substituted with phenyl, or a phenyl group substituted with a naphthyl group, and R103 and R104 are the same as or different from each other, and a dibenzofuran group or It may be a dibenzothiophene group.

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

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

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

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

2 shows an organic light emitting device in which an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 are sequentially stacked on a substrate 1 The structure is illustrated. In such a structure, the compound may be included in the hole injection layer 5, the hole transport layer 6, the light emitting layer 7, or the electron transport layer 8. 2, the hole transport layer 6 may be a single layer or a multi-layer structure of two or more layers. When the hole transport layer has a multi-layer structure, the layer adjacent to the light emitting layer may perform an electron blocking role.

For example, the organic light emitting device according to the present invention uses a metal vapor deposition (PVD) method, such as sputtering or e-beam evaporation, to have a metal or conductive metal oxide on the substrate or alloys thereof It can be prepared by depositing a to form an anode, and then forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, 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 made by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.

The organic material layer may have a multi-layer structure including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, but is not limited thereto, and may have a single layer structure. In addition, the organic material layer may use a variety of polymer materials to reduce the number of solvent processes (e.g., spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer) rather than deposition. Can be prepared in layers.

The positive electrode material is usually a material having a large work function to facilitate hole injection into the organic material layer. Specific examples of the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of metal and oxide such as ZnO: Al or SnO ₂ : Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

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

The hole-injecting material is a material capable of well injecting holes from the anode at a low voltage, and it is preferable that the high-occupied molecular orbital (HOMO) of the hole-injecting material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based substances. Organic materials, anthraquinones, and polyaniline- and polythiophene-based conductive polymers, but are not limited thereto.

As the hole transport material, a material capable of receiving holes from an anode or a hole injection layer and transporting holes to a light emitting layer is suitable as a material having high mobility for holes. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion, but are not limited thereto.

The light emitting layer may emit red, green, or blue light, and may be made of a phosphorescent material or a fluorescent material. As the light-emitting material, a material capable of emitting light in the visible light region by receiving and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively, is preferably a material having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole compounds; Poly(p-phenylenevinylene) (PPV) polymers; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited to these.

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

The iridium-based complex used as a dopant in the light emitting layer is as follows, but is not limited thereto.

[Ir(piq) ₃ ] [Btp ₂ Ir(acac)]

[Ir(ppy) ₃ ] [Ir(ppy) ₂ (acac)]

[Ir(mpyp) ₃ ] [F ₂ Irpic]

[(F ₂ ppy) ₂ Ir(tmd)] [Ir(dfppz) ₃ ]

　　　

　　　

As the electron transport material, a material capable of receiving electrons from the cathode well and transferring them to the light emitting layer, a material having high mobility for electrons is suitable. Specific examples include the Al complex of 8-hydroxyquinoline; Complexes including Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transport layer may include an additional metal complex in the electron transport material, and for example, a material such as Liq may be mixed. At this time, the electron transport material and the additional metal complex may be mixed in a weight ratio of 3:7 to 7:3.

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

<Synthesis example>

Synthesis Example 1. Synthesis of Compound 1

(1) Synthesis of Intermediate 1-1

Intermediate 1-1 was synthesized according to the following scheme.

<Intermediate 1-1>

In a 2L flask, 1-bromo-2,3-dichlorobenzene (55.0 g, 0.243 mol) and sodium tert-butoxys (72.5 g, 0.755 mol) were added together with 700 mL of toluene and stirred at reflux for 1 hour. After cooling to room temperature, aniline (45.1 g, 0.485 mol) was added and heated. Tris(dibenzylideneacetone)dipalladium dissolved in 30mL of toluene after adding 2,2'-bis(diphenylphosphino)-1,1'-binaphthalene (rac-BINAP) (6.06g, 9.74mmole) (0) (4.46 g, 0.284 mol) was slowly added dropwise. After the reaction was completed, the mixture was cooled to room temperature, extracted with ethyl acetate and water, and the organic layer obtained was treated with anhydrous magnesium sulfate, filtered and concentrated to obtain a target product. <Intermediate 1-1> (36.0g, yield 50%) was obtained by column chromatography using ethylacetate and hexane.

Mass [M+1] = 295

(2) Synthesis of Intermediate 1-2

Intermediate 1-2 was synthesized according to the following scheme.

<Intermediate 1-1> <Intermediate 1-2>

In a 2L flask, <Intermediate 1-1> (24.0g, 0.081mol) and sodium tert-butoxys (15.7g, 0.163mol) were added together with 700mL of toluene and refluxed for 1 hour and stirred. After cooling to room temperature, bis(3-bromophenyl)methane (27.1 g, 0.083 mol) was added and heated up to reflux. 2-dicyclohexylphosphino-2,4,6'-triisopropylbiphenyl (XPhos) (3.11g, 6.51mmole) was added and tris(dibenzylideneacetone)dipalladium dissolved in 30mL of toluene (0 ) (2.98 g, 0.040 mol) was slowly added dropwise. After the reaction was completed, the mixture was cooled to room temperature, extracted with ethyl acetate and water, and the organic layer obtained was treated with anhydrous magnesium sulfate, filtered and concentrated to obtain a target product. <Intermediate 1-2> (12.0 g, yield 32%) was obtained by column chromatography using ethyl acetate and hexane.

Mass [M+1] = 459

(3) Synthesis of Intermediate 1-3

Intermediate 1-3 was synthesized according to the following scheme.

<Intermediate 1-1> <Intermediate 1-3>

Using the same method as in (2) of Synthesis Example 1, using <Intermediate 1-1> (15.0 g, 0.051 mol) and 3,3'-sulfonylbis (bromobenzene) (19.5 g, 0.052 mol) <Intermediate 1-3> was obtained (8.5 g, yield 33%).

Mass [M+1] = 509

(4) Synthesis of Intermediate 1-4

Intermediates 1-4 were synthesized according to the following scheme.

<Intermediate 1-3> <Intermediate 1-2> <Intermediate 1-4>

Dissolve <Intermediate 1-2> (6.5g, 0.014mol) and <Intermediate 1-3> (7.0g, 0.014mol) in a 0.25L flask in 50mL of 1,4-dioxane and dissolve potassium bis(trimethylsilyl)amide at room temperature. 0.5M toluene (68.8 mL, 0.034 mol) was slowly added dropwise. The temperature of the reactant was raised to about 80°C to complete the reaction. After completion of the reaction, the temperature was lowered to room temperature, and the organic layer obtained by extraction with ethyl acetate and dilute ammonium chloride aqueous solution was treated with anhydrous magnesium sulfate, filtered, and concentrated to obtain the target product. <Intermediate 1-4> (5.3 g, yield 43%) was obtained by column chromatography using ethyl acetate and hexane.

Mass [M+1] = 901

(5) Synthesis of Compound 1

Compound 1 was synthesized according to the following scheme.

<Intermediate 1-4> <Compound 1>

After adding <Intermediate 1-4> (13.0g, 0.014mol) and 65ml of tert-butylbenzene under nitrogen using a 0.25L flask, the temperature was lowered to -78°C and tert-butyl lithium 1.7M pentane (10.2ml, 0.017 mol) was slowly added dropwise. After the dropping was completed, the temperature of the reactant was raised to 100°C and stirred for 2 hours. The reaction solution was again cooled to -30°C, and boron tribromide (3.68 g, 0.015 mol) was slowly added dropwise. After 30 minutes, the reaction was transferred to an ice bath and N,N'-diisopropylethylamine (6.28ml, 0.036mole) was added, and the temperature was raised to 120°C and stirred for 5 hours. After the reaction was completed, the reactant was cooled to room temperature, neutralized with an aqueous sodium acetate solution, and then the organic layer obtained by extraction with ethyl ethyl acetate was treated with anhydrous magnesium sulfate, filtered and concentrated to obtain a target product. This was purified by column chromatography using tetrahydroturanchi and normal hexane to obtain <Compound 1> (2.6 g, yield 21%).

Mass [M+1] = 849

Synthesis Example 2. Synthesis of Compound 2

Compound 2 was synthesized in the same manner as in Synthesis Example 1, except that 4-tertbutylaniline was used instead of aniline in the synthesis step of Intermediate 1-1.

Mass [M+1] = 1073

Synthesis Example 3. Synthesis of Compound 7

(1) Synthesis of Intermediate 3-1

Intermediate 3-1 was synthesized according to the following scheme.

<Intermediate 3-1>

5-(tert-butyl)-2-chloro-1,3-difluorobenzene (0.147 mol, 30.0 g) was dissolved in 800 mL of dimethylformaldehyde (DMF) and then sodium-tert-butoxide (NatBuO) (0.735 mol) , 70.6g) and 3,3'-methylene diphenol (0.368 mol, 73.6g) were added and stirred at 120°C. After the reaction was completed after 20 hours, the mixture was cooled to room temperature, stopped with a saturated aqueous ammonium chloride solution, and poured into a solution to precipitate a solid. The precipitated solid was filtered and dried with normal hexane, and then the impure target obtained by dissolving in ethyl acetate was purified by column chromatography with an ethyl acetate/normal nucleic acid solvent to obtain 11.0 g (21% yield) of Intermediate 3-1.

(2) Synthesis of Intermediate 3-2

Intermediate 3-2 was synthesized according to the following scheme.

<Intermediate 3-2>

Intermediate 3- in the same manner as in Synthesis Example 3-(1), except that 3,3'-sulfonyldiphenol was used instead of 3,3'-methylenediphenol in the synthesis step of Synthesis Example 3-(1). 2 was synthesized.

(3) Synthesis of Intermediate 3-3

Intermediate 3-3 was synthesized according to the following scheme.

<Intermediate 3-1> <Intermediate 3-2> <Intermediate 3-3>

The same method as in Synthesis Example 1-(4), except that Intermediate 3-1 and Intermediate 3-2 were used instead of Intermediate 1-2 and Intermediate 1-3 in the synthesis step of Synthesis Example 1-(4). Intermediate 3-3 was synthesized.

(4) Synthesis of Compound 7

Compound 7 was synthesized according to the following scheme.

       <Intermediate 3-3> <Compound 7>

Compound 7 was synthesized in the same manner as in Synthesis Example 1-(5), except that Intermediate 3-3 was used instead of Intermediate 1-4 in the synthesis step of Synthesis Example 1-(5).

Mass [M+1] = 661

Synthesis Example 4. Synthesis of Compound 15

(1) Synthesis of Intermediate 4-1

Intermediate 4-1 was synthesized according to the following scheme.

<Intermediate 4-1>

In the synthesis step of Synthesis Example 3-(1), 2-chloro-1,3-difluorobenzene was used instead of 5-(tert-butyl)-2-chloro-1,3-difluorobenzene. Intermediate 4-1 was synthesized in the same manner as in Synthesis Example 3-(1) except for the above.

(2) Synthesis of Intermediate 4-2

Intermediate 4-2 was synthesized according to the following scheme.

<Intermediate 4-1> <Intermediate 1-3> <Intermediate 4-2>

Intermediate 4-2 was synthesized in the same manner as in Synthesis Example 1-(4), except that Intermediate 4-1 was used instead of Intermediate 1-2 in the synthesis step of Synthesis Example 1-(4).

(3) Synthesis of Compound 15

Compound 15 was synthesized according to the following scheme.

       <Intermediate 4-2> <Compound 15>

Compound 15 was synthesized in the same manner as in Synthesis Example 1-(5), except that Intermediate 4-2 was used instead of Intermediate 1-4 in the synthesis step of Synthesis Example 1-(5).

Mass [M+1] = 669

<Example>

Example 1.

A glass substrate (corning 7059 glass) coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 Å was put in distilled water in which a dispersing agent was dissolved and washed with ultrasonic waves. As a detergent, a product of Fischer Co. was used, and distilled water was Millipore Co. Distilled water, which was second filtered as a product filter, was used. After washing the ITO for 30 minutes, the ultrasonic cleaning was repeated 10 times with distilled water for 10 minutes. After washing with distilled water, ultrasonic cleaning was performed in the order of isopropyl alcohol, acetone, and methanol, followed by drying.

On the prepared ITO transparent electrode, HAT was thermally vacuum-deposited to a thickness of 50 Pa to form a hole injection layer. Then, the following HT-A 1000- was vacuum-deposited as a hole transport layer, and subsequently HT-B 100Å was deposited. The light emitting layer was doped with H-A and compound 1 at 2 to 10 wt% as a host, and vacuum deposited to a thickness of 200 mm 2. Subsequently, 300-of ET-A and Liq were deposited at a 1:1 ratio, and subsequently, 150 은 thick silver (Ag) 10 wt% doped magnesium (Mg) and 1,000 Å thick aluminum were deposited to form a cathode. Thus, an organic light emitting device was manufactured.

In the above process, the deposition rate of the organic material was maintained at 1 Å/sec, LiF was 0.2 Å/sec, and aluminum was maintained at a deposition rate of 3 Å/sec to 7 Å/sec.

Example 2.

In Example 1, an organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 2 was used instead of Compound 1.

Example 3.

In Example 1, an organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 7 was used instead of Compound 1.

Example 4.

In Example 1, an organic light emitting device was manufactured according to the same method as Example 1 except for using Compound 15 instead of Compound 1.

Example 5.

An organic light emitting device was manufactured in the same manner as in Example 1, except that H-B was used instead of H-A in Example 1.

Example 6.

An organic light emitting device was manufactured in the same manner as in Example 2, except that H-B was used instead of H-A in Example 2.

Example 7.

An organic light emitting device was manufactured in the same manner as in Example 3, except that H-B was used instead of H-A in Example 3.

Example 8.

An organic light emitting device was manufactured in the same manner as in Example 4, except that H-B was used instead of H-A in Example 4.

Example 9.

An organic light emitting device was manufactured in the same manner as in Example 1, except that H-C was used instead of H-A in Example 1.

Example 10.

An organic light emitting device was manufactured in the same manner as in Example 2, except that H-C was used instead of H-A in Example 2.

Example 11.

An organic light emitting device was manufactured in the same manner as in Example 3, except that H-C was used instead of H-A in Example 3.

Example 12.

An organic light emitting device was manufactured in the same manner as in Example 4, except that H-C was used instead of H-A in Example 4.

<Comparative Example>

Comparative Example 1.

An organic light emitting diode was manufactured according to the same method as Example 1 except for using D-1 instead of Compound 1 in Example 1.

Comparative Example 2.

An organic light emitting diode was manufactured according to the same method as Example 1 except for using D-2 instead of Compound 1 in Example 1.

Comparative Example 3.

An organic light emitting diode was manufactured according to the same method as Example 1 except for using D-3 instead of Compound 1 in Example 1.

Comparative Example 4.

An organic light emitting device was manufactured in the same manner as in Comparative Example 1, except that H-B was used instead of H-A in Comparative Example 1.

Comparative Example 5.

An organic light emitting device was manufactured in the same manner as in Comparative Example 2, except that H-B was used instead of H-A in Comparative Example 2.

Comparative Example 6.

An organic light emitting device was manufactured in the same manner as in Comparative Example 3, except that H-B was used instead of H-A in Comparative Example 3.

Comparative Example 7.

An organic light emitting device was manufactured in the same manner as in Comparative Example 1, except that H-C was used instead of H-A in Comparative Example 1.

Comparative Example 8.

An organic light emitting device was manufactured in the same manner as in Comparative Example 2, except that H-C was used instead of H-A in Comparative Example 2.

Comparative Example 9.

An organic light emitting device was manufactured in the same manner as in Comparative Example 3, except that H-C was used instead of H-A in Comparative Example 3.

The driving voltage and luminous efficiency of the organic light-emitting devices of Examples 1 to 12 and Comparative Examples 1 to 9 were measured at a current density of 10 mA/cm ² , and the time to be 95% of the initial luminance at a current density of 20 mA/cm ² . (LT95) was measured. The results are shown in Table 1 below.

Example Host Dopant @ 10 mA/cm ² @ 20 mA/cm ² Voltage (V) Efficiency (cd/A) CIE y Life (hr) Example 1 H-A Compound 1 4.3 6.25 0.040 145 Example 2 H-A Compound 2 4.2 6.51 0.039 180 Example 3 H-A Compound 7 4.3 6.40 0.043 170 Example 4 H-A Compound 15 4.5 6.35 0.041 165 Example 5 H-B Compound 1 4.2 6.30 0.040 140 Example 6 H-B Compound 2 4.2 6.62 0.039 170 Example 7 H-B Compound 7 4.3 6.43 0.043 165 Example 8 H-B Compound 15 4.3 6.30 0.041 180 Example 9 H-C Compound 1 4.4 6.20 0.040 175 Example 10 H-C Compound 2 4.3 6.45 0.039 240 Example 11 H-C Compound 7 4.3 6.50 0.043 190 Example 12 H-C Compound 15 4.5 6.42 0.041 230 Comparative Example 1 H-A D-1 4.6 6.10 0.043 140 Comparative Example 2 H-A D-2 4.6 5.20 0.042 130 Comparative Example 3 H-A D-3 4.7 6.10 0.040 120 Comparative Example 4 H-B D-1 4.4 6.00 0.043 110 Comparative Example 5 H-B D-2 4.5 5.70 0.042 80 Comparative Example 6 H-B D-3 4.5 5.10 0.040 100 Comparative Example 7 H-C D-1 4.7 5.10 0.042 110 Comparative Example 8 H-C D-2 4.6 5.00 0.042 90 Comparative Example 9 H-C D-3 4.6 4.70 0.041 110

According to Table 1, when comparing Examples 1 to 12 and Comparative Examples 1 and 9 using the same host material, it can be seen that the Examples have lower driving voltage, higher efficiency, and superior life characteristics compared to Comparative Examples. Through the above, the preferred embodiment (light emitting layer) of the present specification has been described, but the present invention is not limited thereto, and can be implemented by various modifications within the scope of the claims and the detailed description of the invention. Belongs to the category of

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

Claims (8)

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

In Chemical Formula 1,
A1 and A2 are the same as or different from each other, and each independently an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylamine group having 12 to 30 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms, and carbon atoms A benzene ring substituted or unsubstituted with 1 or 2 substituents selected from the group consisting of a heterocyclic group having 2 to 30 carbon atoms unsubstituted or substituted with an alkyl group of 1 to 20,
X, Y, Z and W are the same as or different from each other, and each independently is O or NRa,
Ra is an alkyl group having 1 to 20 carbon atoms; Or an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms,
R ₁ to R ₁₂ are hydrogen. The method according to claim 1,
Formula 1 is a compound represented by the following formula (2):
[Formula 2]

In Chemical Formula 2,
X, Y, Z and W are the same as defined in Formula 1,
R ₂₁ , R ₂₃ , R ₂₄ and R ₂₆ are hydrogen,
R ₂₂ and R ₂₅ are the same as or different from each other, and each independently hydrogen; An alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylamine group having 12 to 30 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms, or a carbon number unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms. 2 to 30 heterocyclic groups,
n1 to n6 are each an integer of 0 to 2, and when n1 to n6 are each 2, the substituents in parentheses are the same or different. The method according to claim 1,
A1 and A2 are the same as or different from each other, and each independently substituted with a methyl group, ethyl group, propyl group, isopropyl group, butyl group, tert-butyl group, phenyl group, biphenyl group, naphthyl group, diphenylamine group, or tert-butyl group Diphenylamine group, carbazole group, carbazole group substituted with tert-butyl group, phenoxazinyl group (phenoxazine), and

A compound which is a benzene ring unsubstituted or substituted with 1 or 2 substituents selected from the group consisting of. The method according to claim 1,
The compound represented by Formula 1 is any one selected from the following compounds:

Compound 1 Compound 2

Compound 4 Compound 5 Compound 6

Compound 7 Compound 8 Compound 9

Compound 10 Compound 11

Compound 13 Compound 14 Compound 15

Compound 16 Compound 17 Compound 18

Compound 21

Compound 22 Compound 23. A first electrode; A second electrode provided opposite to the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein one or more of the organic material layers comprises a compound according to any one of claims 1 to 4 Light emitting element. The method according to claim 5,
The organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer comprises the compound. The method according to claim 5,
The organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or electron injection layer comprises the compound. The method according to claim 5,
The organic material layer includes an emission layer, and the emission layer includes the compound.

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