WO2020159279A1

WO2020159279A1 - Polycyclic compound and organic light-emitting element comprising same

Info

Publication number: WO2020159279A1
Application number: PCT/KR2020/001480
Authority: WO
Inventors: 윤정민; 김공겸; 구기동; 김영석; 이민우; 오중석
Original assignee: 주식회사 엘지화학
Priority date: 2019-02-01
Filing date: 2020-01-31
Publication date: 2020-08-06
Also published as: KR102453982B1; CN112912370A; KR20200096158A

Abstract

The present specification provides a compound represented by chemical formula 1 and an organic light-emitting element comprising same.

Description

Polycyclic compound and organic light emitting device including same

This specification claims the filing date benefit of Korean Patent Application No. 10-2019-0013525 filed with the Korean Patent Office on February 1, 2019, all of which is included in this specification.

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 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 excitons are formed when the injected holes meet the electrons. When it falls to the ground again, it will shine.

Most of the materials used in the organic light emitting device are pure organic materials or complex compounds in which organic materials and metals are complexed. Materials used in the organic light emitting device may be divided into a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc. according to the use. Here, as the hole injection material or the hole transport material, an organic material having a p-type property, that is, an organic material that is easily oxidized and has an electrochemically stable state during oxidation is mainly used. On the other hand, as an electron injection material or an electron transport material, an organic material having n-type properties, that is, an organic material that is easily reduced and has an electrochemically stable state during reduction, is mainly used. The light emitting layer material is preferably a material having both p-type and n-type properties, that is, a material having a stable form in both the oxidation and reduction states, and a material having high luminous efficiency that converts it to light when excitons are formed. desirable.

In order to sufficiently exhibit the excellent characteristics of the above-described organic light emitting device, the development of a material forming an organic material layer in the device is continuously required.

(Patent Document 1) Korean Patent Publication No. 10-2016-034804

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,

X is O, S or Si,

Ar ₁ to Ar ₄ 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 cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group; Or combine with adjacent groups to form a substituted or unsubstituted carbazole,

R ₁ to R ₈ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, at least one of R ₁ to R ₈ is deuterium; Halogen group; Cyano group; Nitro group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In addition, the present invention is a first electrode; A second electrode; And one or more organic material layers provided between the first electrode and the second electrode, and at least one layer of the organic material layer includes a compound represented by Chemical Formula 1.

The compound described in the present specification is not only easy to manufacture, but when it is included as a material of an organic material layer of an organic light emitting device, an organic light emitting device having a low driving voltage and excellent efficiency and lifetime characteristics can be obtained.

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 It is done.

1: Substrate

2: anode

3: light emitting layer

4: Cathode

5: hole injection layer

6: hole transport layer

7: emitting layer

8: electron transport layer

Hereinafter, this specification will be described in more detail.

The present specification provides a compound represented by Formula 1 below. The compound represented by the following formula (1) is not only easier to manufacture than the core structure in which the amine group is substituted at another position, but also because two amine groups are bonded at a specific position of the 5-ring condensed heterocycle, it is an excellent device when applied to an organic light emitting device. A device having efficiency, luminous efficiency, and life characteristics can be obtained.

In addition, according to an exemplary embodiment of the present specification, when the compound represented by the following formula (1) is applied as a dopant in a light emitting layer in an organic light emitting device, energy transfer with a host is easy, so a device having high luminous efficiency and long life characteristics Can get In Formula 1, a compound containing one amine group or not containing it is not only suitable for use as a dopant in the light emitting layer, but also has a very low luminous efficiency when applied to a device. Since the condensation position of the amine ring bonded to the amine group in Chemical Formula 1 has a higher quantum efficiency (QE) than a compound different from the compound, there is an advantage of showing high luminous efficiency when applied to a device.

In addition, the compound represented by the following formula (1), by including a substituent other than one or more hydrogen in a 5-membered condensed heterocycle, it is possible to obtain a device that is electronically stable and has excellent life characteristics when applied to a device, and is applied as a dopant in a light emitting layer. It is easy to control the time wavelength and shows excellent luminous efficiency and color.

[Formula 1]

In Chemical Formula 1,

X is O, S or Si,

In the present specification, when a part “includes” 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 the substituent in this specification 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" in this specification is deuterium; Halogen group; Cyano group (-CN); Nitro group; Hydroxy group; Silyl group; Boron group; Alkyl groups; Alkenyl group; Alkynyl group; Alkoxy groups; Aryloxy group; Cycloalkyl group; Aryl group; And 1 or 2 or more substituents selected from the group consisting of heterocyclic groups, or substituted with two or more substituents among the above-exemplified substituents, or having no substituents. The'substituent to which two or more substituents are connected' may be a phenylnaphthyl group. That is, the phenyl naphthyl group may be an aryl group or may be interpreted as a phenyl group substituted with a naphthyl group.

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

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

In the present specification, the silyl group may be represented by the formula of -SiY _a Y _b Y _c , wherein Y _a , Y _b and Y _c are each hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or it may be a substituted or unsubstituted aryl group. The silyl group specifically includes, but is not limited to, trimethylsilyl group, triethylsilyl group, tert-butyldimethylsilyl group, ethyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like. Does not.

In the present specification, the boron group may be represented by the formula of -BY _d Y _e , wherein Y _d and Y _e are each hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or it may be a substituted or unsubstituted aryl group. The boron group is specifically dimethyl boron group, diethyl boron group, tert-butyl methyl boron group, diphenyl boron group, phenyl boron group, and the like, but is not limited thereto.

In the present specification, the number of carbon atoms in the alkyl group is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the alkyl group has 1 to 30 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms.

Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, etc., and the alkyl group may be a straight chain or a branched chain, and according to an example, the profile The group includes n-propyl group and isopropyl group, and the butyl group includes n-butyl group, isobutyl group and ter-butyl group.

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

) And the like, but is not limited thereto.

In this specification, the alkyl group of the alkoxy group can be applied to the description of the alkyl group described above.

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, a quarterphenyl 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, perylene group, triphenyl group, chrysenyl group, fluorenyl group, fluoranthenyl group, triphenylenyl group, etc. , 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.

When the fluorenyl group is substituted,

,

,

Spirofluorenyl groups, such as (spira adamantane fluorene);

(9,9-dimethylfluorenyl group), and

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

In the present specification, the heterocyclic group is a hetero atom and is a ring group containing at least one of N, O, S, Si, and Se, and carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms. According to an exemplary embodiment, the heterocyclic group has 2 to 30 carbon atoms. Examples of the heterocyclic group include pyridyl group; Quinoline group; Thiophene group; Dibenzothiophene group; Furan group; Dibenzofuran group; Naphthobenzofuran group; Carbazole; Benzocarbazole group; Naphthobenzothiophene groups, and the like, but are not limited to these.

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

In the present specification, the hydrocarbon ring may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and the aromatic hydrocarbon ring may be applied to the description of the aryl group described above except that it is divalent, and the aliphatic hydrocarbon ring is 2 A description of the cycloalkyl group described above may be applied, except for Ca.

According to an exemplary embodiment of the present specification, X is O, S or Si. When X is O, S, or Si, X has a superior thermal stability than a compound having C, and thus has an advantage of being easy to sublimation purification and device deposition, thereby improving the lifespan characteristics of the device.

According to one embodiment of the present specification, R ₁ to R ₈ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, at least one of R ₁ to R ₈ is deuterium; Halogen group; Cyano group; Nitro group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

According to another exemplary embodiment, R ₁ to R ₈ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms; A cycloalkyl group having 3 to 30 carbon atoms; Or an aryl group having 6 to 30 carbon atoms, and at least one of R ₁ to R ₈ is deuterium; A substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms; A cycloalkyl group having 3 to 30 carbon atoms; Or an aryl group having 6 to 30 carbon atoms.

In another exemplary embodiment, R ₁ to R ₈ 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 cycloalkyl group having 3 to 30 carbon atoms, at least one of R ₁ to R ₈ is deuterium; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms.

According to another exemplary embodiment, R ₁ to R ₈ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted ethyl group; A substituted or unsubstituted isopropyl group; A substituted or unsubstituted tert-butyl group; A substituted or unsubstituted cyclopentyl group; Or a substituted or unsubstituted cyclohexyl group, at least one of R ₁ to R ₈ is deuterium; A substituted or unsubstituted ethyl group; A substituted or unsubstituted isopropyl group; A substituted or unsubstituted tert-butyl group; A substituted or unsubstituted cyclopentyl group; Or a substituted or unsubstituted cyclohexyl group.

In another exemplary embodiment, R ₁ to R ₈ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Ethyl group; Isopropyl group; tert-butyl group; Cyclopentyl group; Or a cyclohexyl group, wherein at least one of R ₁ to R ₈ is deuterium; Ethyl group; Isopropyl group; tert-butyl group; Cyclopentyl group; Or a cyclohexyl group.

According to an exemplary embodiment of the present specification, at least one of R ₁ and R ₆ is deuterium; Halogen group; Cyano group; Nitro group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted hetero ring, the rest is hydrogen.

According to another exemplary embodiment, at least one of R ₁ and R ₆ is deuterium; A substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms; A cycloalkyl group having 3 to 30 carbon atoms; Or an aryl group having 6 to 30 carbon atoms, the rest is hydrogen.

According to another exemplary embodiment, at least one of R ₁ and R ₆ is deuterium; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, the rest is hydrogen.

According to another exemplary embodiment, at least one of R ₁ and R ₆ is deuterium; A substituted or unsubstituted ethyl group; A substituted or unsubstituted isopropyl group; A substituted or unsubstituted tert-butyl group; A substituted or unsubstituted cyclopentyl group; Or a substituted or unsubstituted cyclohexyl group, the rest is hydrogen.

According to another exemplary embodiment, at least one of R ₁ and R ₆ is deuterium; Ethyl group; Isopropyl group; tert-butyl group; Cyclopentyl group; Or a cyclohexyl group, the rest being hydrogen.

In another exemplary embodiment, R ₁ is deuterium; Ethyl group; Isopropyl group; tert-butyl group; Cyclopentyl group; Or a cyclohexyl group.

According to another exemplary embodiment, R ₆ is deuterium; Ethyl group; Isopropyl group; tert-butyl group; Cyclopentyl group; Or a cyclohexyl group.

In another exemplary embodiment, R ₁ and R ₆ are the same as or different from each other, and each independently deuterium; Ethyl group; Isopropyl group; tert-butyl group; Cyclopentyl group; Or a cyclohexyl group.

According to the exemplary embodiment of the present specification, Ar ₁ to Ar ₄ 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 cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 40 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a heterocyclic group containing O, S or N as a substituted or unsubstituted hetero atom having 2 to 60 carbon atoms; Or it combines with adjacent groups to form a substituted or unsubstituted carbazole.

In another exemplary embodiment, Ar ₁ to Ar ₄ 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 60 carbon atoms; Or a heterocyclic group containing O, S or N as a substituted or unsubstituted hetero atom having 2 to 60 carbon atoms; Or it combines with adjacent groups to form a substituted or unsubstituted carbazole.

In another exemplary embodiment, Ar ₁ to Ar ₄ are the same as or different from each other, and each independently an alkyl group having 1 to 20 carbon atoms; 6 to 6 carbon atoms unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen groups, cyano groups, alkyl groups having 1 to 20 carbon atoms, trialkylsilyl groups having 3 to 20 carbon atoms, and cycloalkyl groups having 3 to 30 carbon atoms. 60 aryl group; Or carbon number substituted or unsubstituted with one or more substituents selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, and an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms. A heterocyclic group containing O, S or N as a hetero atom of 2 to 60; Alternatively, adjacent groups are combined with each other to form a carbazole substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms.

According to another exemplary embodiment, Ar ₁ to Ar ₄ are the same as or different from each other, and each independently substituted or unsubstituted ethyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted benzofluorenyl group; A substituted or unsubstituted spiroadamantanefluorenyl group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted carbazole group; Or Ar ₁ and Ar ₂ ; And Ar ₃ And Ar ₄ One or more selected from the group consisting of each other to form a substituted or unsubstituted carbazole. The "substituted or unsubstituted" is deuterium, halogen group, cyano group, straight or branched alkyl group having 1 to 20 carbon atoms, trialkylsilyl group having 1 to 20 carbon atoms, cycloalkyl group having 3 to 30 carbon atoms, and 6 to 6 carbon atoms. It means that it is unsubstituted or substituted with one or more substituents selected from the group consisting of 30 aryl groups.

In another exemplary embodiment, Ar ₁ to Ar ₄ are the same as or different from each other, and each independently substituted or unsubstituted ethyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted benzofluorenyl group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted carbazole group; Or Formula A: Or it combines with adjacent groups to form a substituted or unsubstituted carbazole. The "substituted or unsubstituted" is deuterium, halogen group, cyano group, straight or branched alkyl group having 1 to 20 carbon atoms, trialkylsilyl group having 3 to 20 carbon atoms, cycloalkyl group having 3 to 30 carbon atoms, and 6 to 6 carbon atoms. It means that it is unsubstituted or substituted with one or more substituents selected from the group consisting of 30 aryl groups.

[Formula A]

In Chemical Formula A,

R ₃₀ is hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

n1 is an integer from 0 to 7, and when n1 is 2 or more, 2 or more R ₃₀ are the same as or different from each other,

Means the position to be joined.

According to another exemplary embodiment, Ar ₁ to Ar ₄ are the same as or different from each other, and each independently an ethyl group; A phenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen, cyano, methyl, isopropyl, tert-butyl, trimethylsilyl, cyclopentyl and cyclohexyl groups; A biphenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen, cyano, methyl, isopropyl, tert-butyl, trimethylsilyl, cyclopentyl and cyclohexyl groups; A terphenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen, cyano, methyl, isopropyl, tert-butyl, trimethylsilyl, cyclopentyl and cyclohexyl groups; A naphthyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen, cyano, methyl, isopropyl, tert-butyl, trimethylsilyl, cyclopentyl and cyclohexyl groups; A phenanthrenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen, cyano, methyl, isopropyl, tert-butyl, trimethylsilyl, cyclopentyl and cyclohexyl groups; A fluorenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen, cyano, methyl, isopropyl, tert-butyl, trimethylsilyl, cyclopentyl and cyclohexyl groups; A benzofluorenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen, cyano, methyl, isopropyl, tert-butyl, trimethylsilyl, cyclopentyl and cyclohexyl groups; A spiroadamantanfluorenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen, cyano, methyl, tert-butyl, trimethylsilyl, cyclopentyl and cyclohexyl groups; A dibenzofuran group unsubstituted or substituted with one or more substituents selected from the group consisting of a methyl group, tert-butyl group, tert-butylphenyl group, cyclopentyl group, and cyclohexyl group; A dibenzothiophene group unsubstituted or substituted with one or more substituents selected from the group consisting of a methyl group, tert-butyl group, tert-butylphenyl group, cyclopentyl group, and cyclohexyl group; Or a carbazole group unsubstituted or substituted with one or more substituents selected from the group consisting of a methyl group, tert-butyl group, tert-butylphenyl group, cyclopentyl group and cyclohexyl group; Or Ar ₁ and Ar ₂ ; And Ar ₃ And Ar ₄ One or more selected from the group consisting of combines with each other to form a carbazole unsubstituted or substituted with a butyl group.

According to the exemplary embodiment of the present specification, Ar ₁ to Ar ₄ are the same as or different from each other, and each independently selected from an alkyl group having 1 to 10 carbon atoms, and the following structures, or bonded to each other with adjacent groups to be substituted or unsubstituted Form carbazole.

In the above structures,

W is O, S or NR ₁₀₃ ,

R ₁₀₁ to R ₁₀₃ 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,

The structures are deuterium; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; And one or more substituents selected from the group consisting of substituted or unsubstituted aryl groups,

In the above structures,

Means the position to be joined.

According to an exemplary embodiment of the present specification, the structures are deuterium, a halogen group, a cyano group, a trialkylsilyl group having 3 to 20 carbon atoms, a linear or branched alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, and It may be further substituted with one or more substituents selected from the group consisting of aryl groups having 6 to 30 carbon atoms.

According to another exemplary embodiment, the structures are one or more substituents selected from the group consisting of deuterium, halogen, cyano, trimethylsilyl, methyl, isopropyl, tert-butyl, cyclopentyl and cyclohexyl groups It may be further substituted with.

According to one embodiment of the present specification, R ₁₀₁ to R ₁₀₃ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

In another exemplary embodiment, R ₁₀₁ to R ₁₀₃ 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, R ₁₀₁ to R ₁₀₃ 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; Or an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms.

In another exemplary embodiment, R ₁₀₁ to R ₁₀₃ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Methyl group; Isopropyl group; tert-butyl group; Or a phenyl group unsubstituted or substituted with tert-butyl group.

According to one embodiment of the present specification, -N(Ar ₁ )(Ar ₂ ) and -N(Ar ₃ )(Ar ₄ ) are the same as or different from each other, and each independently represents the following Chemical Formula 1-A or 1-B It is indicated by.

[Formula 1-A]

[Formula 1-B]

In Chemical Formulas 1-A and 1-B,

R ₁₁ and 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 cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R ₂₀ to R ₂₇ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

In the above structures,

Means the position to be joined.

According to the exemplary embodiment of the present specification, R ₁₁ and 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 cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 40 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a heterocyclic group containing O, S or N as a substituted or unsubstituted hetero atom having 2 to 60 carbon atoms.

In another exemplary embodiment, R ₁₁ and 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 60 carbon atoms; Or a heterocyclic group containing O, S or N as a substituted or unsubstituted hetero atom having 2 to 60 carbon atoms.

In another exemplary embodiment, R ₁₁ and R ₁₂ are the same as or different from each other, and each independently an alkyl group having 1 to 20 carbon atoms; Deuterium, halogen group, cyano group, alkyl group having 1 to 20 carbon atoms, trialkylsilyl group having 3 to 20 carbon atoms, and 3 to 3 carbon atoms unsubstituted or substituted with one or more substituents selected from the group consisting of cycloalkyl groups having 3 to 30 carbon atoms. 60 aryl group; Or carbon number substituted or unsubstituted with one or more substituents selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, and an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms. It is a heterocyclic group containing O, S or N as heterogeneous elements of 2 to 60.

According to another exemplary embodiment, R ₁₁ and R ₁₂ are the same as or different from each other, and each independently substituted or unsubstituted ethyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted benzofluorenyl group; A substituted or unsubstituted spiroadamantanefluorenyl group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted carbazole group.

According to another exemplary embodiment, R ₁₁ and R ₁₂ are the same as or different from each other, and each independently an ethyl group; A phenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen, cyano, methyl, isopropyl, tert-butyl, trimethylsilyl, cyclopentyl and cyclohexyl groups; A biphenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen, cyano, methyl, isopropyl, tert-butyl, trimethylsilyl, cyclopentyl and cyclohexyl groups; A terphenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen, cyano, methyl, isopropyl, tert-butyl, trimethylsilyl, cyclopentyl and cyclohexyl groups; A naphthyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen, cyano, methyl, isopropyl, tert-butyl, trimethylsilyl, cyclopentyl and cyclohexyl groups; A phenanthrenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen, cyano, methyl, isopropyl, tert-butyl, trimethylsilyl, cyclopentyl and cyclohexyl groups; A fluorenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen, cyano, methyl, isopropyl, tert-butyl, trimethylsilyl, cyclopentyl and cyclohexyl groups; A benzofluorenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen, cyano, methyl, isopropyl, tert-butyl, trimethylsilyl, cyclopentyl and cyclohexyl groups; Spiroadamantane fluoride substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, halogen, cyano, methyl, isopropyl, tert-butyl, trimethylsilyl, cyclopentyl and cyclohexyl groups Neil group; A dibenzofuran group unsubstituted or substituted with one or more substituents selected from the group consisting of a methyl group, tert-butyl group, tert-butylphenyl group, cyclopentyl group, and cyclohexyl group; A dibenzothiophene group unsubstituted or substituted with one or more substituents selected from the group consisting of a methyl group, tert-butyl group, tert-butylphenyl group, cyclopentyl group, and cyclohexyl group; Or a carbazole group unsubstituted or substituted with one or more substituents selected from the group consisting of a methyl group, tert-butyl group, tert-butylphenyl group, cyclopentyl group, and cyclohexyl group.

According to an exemplary embodiment of the present specification, the R _{20 To} R _{27 Are} the same as or different from each other, each independently hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

According to another exemplary embodiment, R ₂₀ to R ₂₇ are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted tert-butyl group.

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

[Formula 1-1]

[Formula 1-2]

In Chemical Formulas 1-1 and 1-2,

The definitions of X, R ₁ to R ₈ , and Ar ₁ to Ar ₃ are the same as those in Formula 1,

R ₃₀ and R ₃₀ ′ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

n1 and n1' are each an integer of 0 to 7, and when n1 and n1' are each 2 or more, structures in two or more parentheses are the same or different from each other.

According to an exemplary embodiment of the present specification, the R ₃₀ And R ₃₀ 'is hydrogen.

In one embodiment of the present specification, n1 and n1' are 0 or 1, respectively.

According to one embodiment of the present specification, the -N(Ar ₁ )(Ar ₂ ) and -N(Ar ₃ )(Ar ₄ ) are the same as or different from each other, and each independently represented by one of the following structures.

In the above structures,

Means the position to be joined.

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

The core structure of the compound represented by Formula 1 of the present specification may be prepared as in Reaction Schemes 1 to 4 below, and amine groups may be attached to the following intermediates E-1 to E-4 through an amination reaction known in the art. Can. In addition, additional substituents may be combined by methods known in the art, and the type, location, and number of substituents may be changed according to techniques known in the art.

One)

[Intermediate A-1] [Intermediate B-1]

The intermediate A-1 (56.1 g, 175 mmol) and 3-bromonaphthalene-2,7-diol [3-bromonaphthalene-2,7-diol] (44 g, 184 mmol), K ₂ CO ₃ (145 g, 1050 mmol) ) In 1,4-dioxane/water (4:1) (1500 mL). After reflux stirring, tetrakis-(triphenylphosphine)palladium (TTP) 2g was added, and the mixture was refluxed and stirred for 12 hours. After the reaction was completed, the temperature was lowered to room temperature, and then extracted with water and ethyl acetate to separate the organic layer. The organic layer was treated with anhydrous magnesium sulfate, and then filtered and concentrated under reduced pressure. The solid was recrystallized from chloroform to prepare intermediate B-1. (43.2 g, yield 70%, MS: [M+H] + = 353)

2)

[Intermediate B-1] [Intermediate C-1]

The intermediate B-1 (43.5 g, 135.6 mmol) and CH ₃ SO ₂ OH (60 mL) were added, followed by stirring for 5 hours. After cooling to room temperature, the reactant was poured into water, and the resulting solid was filtered to recrystallize the resulting solid with chloroform and ethanol to prepare the intermediate C-1. (36.3 g, yield 88%, MS:[M+H]+=335)

3)

[Intermediate C-1] [Intermediate D-1]

The intermediate C-1 (36.3 g, 108 mmol) and isopropylboronic acid (10.5 g, 119 mmol), K ₂ CO ₃ (74.6 g, 540 mmol) are 1,4-dioxane/water (4 :1) (1500 mL). 2 g of tetrakis-(triphenylphosphine)palladium (TTP) and DPPF (1,1'-ferrocenediylbis(diphenylphosphine)[1,1'-Ferrocendiylbis(diphenylphosphine)]) under reflux Then, the mixture was stirred at reflux for 12 hours. After the reaction was completed, the temperature was lowered to room temperature, and then extracted with water and ethyl acetate to separate the organic layer. The organic layer was treated with anhydrous magnesium sulfate, and then filtered and concentrated under reduced pressure. The solid was recrystallized from chloroform to prepare intermediate D-1. (19.6 g, yield 53%, MS: [M+H] + = 343)

4)

[Intermediate D-1] [Intermediate E-1]

The intermediate D-1 (19.6 g, 57.3 mmol) was added to tetrahydrofuran (1000 mL), stirred for 1 hour, and then K ₂ CO ₃ (23.7 g, 172 mmol), 1,1,2,2,3, 3,4,4,4-nonafluorobutane-1-sulfonylfluoride[1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride] (52g, 172mmol) After the addition, the mixture was further stirred for 24 hours. After the reaction, water and tetrahydrofuran were further added and extracted to separate the organic layer. The organic layer was treated with anhydrous magnesium sulfate, and then filtered and concentrated under reduced pressure. The solid was recrystallized from chloroform and ethanol to prepare the intermediate E-1. (42.6 g, yield 85%, MS: [M+H] + = 915)

One)

[Intermediate A-1] [Intermediate B-2]

Compound A-1 (56.1 g, 175 mmol) and 3-bromonaphthalene-2,7-diol [3-bromonaphthalene-2,7-diol] (44 g, 184 mmol), K ₂ CO ₃ (145 g, 1050 mmol) ) In 1,4-dioxane/water (4:1) (1500 mL). After reflux stirring, tetrakis-(triphenylphosphine)palladium (TTP) 2g was added, and the mixture was refluxed and stirred for 12 hours. After the reaction was completed, the temperature was lowered to room temperature, and then extracted with water and ethyl acetate to separate the organic layer. The organic layer was treated with anhydrous magnesium sulfate, and then filtered and concentrated under reduced pressure. The solid was recrystallized from chloroform to prepare intermediate B-2. (43.2 g, yield 70%, MS: [M+H] + = 353)

2)

[Intermediate B-2] [Intermediate C-2]

The intermediate B-2 (48.1 g, 124.2 mmol) and CH ₃ SO ₂ OH (70 mL) were added, followed by stirring for 5 hours. After cooling to room temperature, the reactant was poured into water, and the resulting solid was filtered to recrystallize the resulting solid with chloroform and ethanol to prepare the intermediate C-2. (37.1 g, yield 81%, MS:[M+H]+=370)

3)

[Intermediate C-2] [Intermediate D-2]

The intermediate C-2 (37.1 g, 100.6 mmol) and cyclohexylboronic acid (28.3 g, 221.3 mmol), K ₂ CO ₃ (111.2 g, 804.8 mmol) 1,4-dioxane/water ( 4:1) (1500 mL). 4 g of tetrakis-(triphenylphosphine)palladium (TTP) and DPPF (1,1'-ferrocenediylbis(diphenylphosphine)[1,1'-Ferrocendiylbis(diphenylphosphine)]) under reflux stirring Then, the mixture was stirred at reflux for 12 hours. After the reaction was completed, the temperature was lowered to room temperature, and then extracted with water and ethyl acetate to separate the organic layer. The organic layer was treated with anhydrous magnesium sulfate, and then filtered and concentrated under reduced pressure. The solid was recrystallized from chloroform to prepare intermediate D-2. (25.7 g, yield 55%, MS: [M+H] + = 465)

4)

[Intermediate D-2] [Intermediate E-2]

The intermediate D-2 (25.7 g, 55.3 mmol) was added to tetrahydrofuran (1000 mL), stirred for 1 hour, and then K ₂ CO ₃ (23 g, 165.9 mmol), 1,1,2,2,3, 3,4,4,4-nonafluorobutane-1-sulfonylfluoride[1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride] (52g, 172mmol) After the addition, the mixture was further stirred for 24 hours. After the reaction, water and tetrahydrofuran were further added and extracted to separate the organic layer. The organic layer was treated with anhydrous magnesium sulfate, and then filtered and concentrated under reduced pressure. The solid was recrystallized from chloroform and ethanol to prepare the intermediate E-2. (49.6 g, yield 90%, MS:[M+H]+=997)

One)

[Intermediate C-2] [Intermediate D-3]

The intermediate C-2 (37.1 g, 100.6 mmol) and 2,4,4,5,5-pentamethyl-1,3,2-dioxabororan[2,4,4,5,5-pentamethyl-1 ,3,2-dioxaborolane] (31.4 g, 221.3 mmol), K ₂ CO ₃ (111.2 g, 804.8 mmol) was added to 1,4-dioxane/water (4:1) (1500 mL). 4 g of tetrakis-(triphenylphosphine)palladium (TTP) and DPPF (1,1'-ferrocenediylbis(diphenylphosphine)[1,1'-Ferrocendiylbis(diphenylphosphine)]) under reflux agitation Then, the mixture was stirred at reflux for 12 hours. After the reaction was completed, the temperature was lowered to room temperature, and then extracted with water and ethyl acetate to separate the organic layer. The organic layer was treated with anhydrous magnesium sulfate, and then filtered and concentrated under reduced pressure. The solid was recrystallized from chloroform to prepare intermediate D-3. (15.8 g, yield 48%, MS: [M+H] + = 329)

2)

[Intermediate D-3] [Intermediate E-3]

The intermediate D-3 (18.2 g, 55.3 mmol) was added to tetrahydrofuran (1000 mL), stirred for 1 hour, and then K ₂ CO ₃ (23 g, 165.9 mmol), 1,1,2,2,3, 3,4,4,4-nonafluorobutane-1-sulfonylfluoride[1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride] (52g, 172mmol) After the addition, the mixture was further stirred for 24 hours. After the reaction, water and tetrahydrofuran were further added and extracted to separate the organic layer. The organic layer was treated with anhydrous magnesium sulfate, and then filtered and concentrated under reduced pressure. The solid was recrystallized from chloroform and ethanol to prepare the intermediate E-3. (44.9 g, Yield 91%, MS: [M+H] + = 893)

One)

[Intermediate C-2] [Intermediate D-4]

The intermediate C-2 (37.1 g, 100.6 mmol) and 2-isopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane[2-isopropyl-4,4,5, 5-tetramethyl-1,3,2-dioxaborolane] (37.6 g, 221.3 mmol), K ₂ CO ₃ (111.2 g, 804.8 mmol) in 1,4-dioxane/water (4:1) (1500 mL) Input. 4 g of tetrakis-(triphenylphosphine)palladium (TTP) and DPPF (1,1'-ferrocenediylbis(diphenylphosphine)[1,1'-Ferrocendiylbis(diphenylphosphine)]) under reflux agitation Then, the mixture was stirred at reflux for 12 hours. After the reaction was completed, the temperature was lowered to room temperature, and then extracted with water and ethyl acetate to separate the organic layer. The organic layer was treated with anhydrous magnesium sulfate, and then filtered and concentrated under reduced pressure. The solid was recrystallized from chloroform to prepare intermediate D-4. (19.3 g, yield 50%, MS: [M+H] + = 385)

2)

[Intermediate D-4] [Intermediate E-4]

The intermediate D-4 (21.3 g, 55.3 mmol) was added to tetrahydrofuran (1000 mL), stirred for 1 hour, and then K ₂ CO ₃ (23 g, 165.9 mmol), 1,1,2,2,3, 3,4,4,4-nonafluorobutane-1-sulfonylfluoride[1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride](52g, 172mmol) After the addition, the mixture was further stirred for 24 hours. After the reaction, water and tetrahydrofuran were further added and extracted to separate the organic layer. The organic layer was treated with anhydrous magnesium sulfate, and then filtered and concentrated under reduced pressure. The solid was recrystallized from chloroform and ethanol to prepare the intermediate E-4. (44.6 g, yield 85%, MS: [M+H] + = 949)

Compounds having various energy band gaps can be synthesized by introducing various substituents to the compound represented by Chemical Formula 1 above. In addition, in this specification, by introducing various substituents to the core structure of the above structure, it is also possible to control the energy level of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular unorbital (LUMO) of the compound.

In this specification, "energy level" means the amount of energy. Therefore, even when the energy level is displayed in the negative (-) direction from the vacuum level, the energy level is interpreted to mean the absolute value of the corresponding energy value. For example, a HOMO (highest occupied molecular orbital) energy level means a distance from a vacuum level to the highest occupied molecular orbital. In addition, LUMO (lowest unoccupied molecular orbital) energy level means the distance from the vacuum level to the lowest unoccupied molecular orbital.

According to the exemplary embodiment of the present specification, the compound represented by Chemical Formula 1 may have a band gap energy of 2.6 eV to 2.9 eV. The compound has a light-emitting wavelength value suitable for application as a blue dopant in the light-emitting layer of the organic light-emitting device, whereby a device having high efficiency can be obtained. The band gap energy can be measured through the method of Experimental Example 1 described later.

Specifically, the band gap energy (band gap energy) value means the difference between the HOMO (Highest Occupied Molecular Orbital) energy level and the LUMO (Lowest Unoccupied Molecular Orbital) energy level, and the HOMO energy level and the LUMO energy level are as follows: Can be measured.

In order to determine the molecular structure of a chemical, the input structure is optimized using a density functional theory (DFT). For the DFT calculation, the BPW91 calculation method (Becke exchange and Perdew correlation-correlation functional) and the DNP (double numerical basis set including polarization functional) basis set are used. The BPW91 calculation method is presented in the dissertation A. D. Becke, Phys. Rev. A, 38, 3098 (1988) 'and'J. P. Perdew and Y. Wang, Phys. Rev. B, 45, 13244 (1992), and the DNP basal set is thesis'B. Delley, J. Chem. Phys., 92, 508 (1990).

Biovia's'DMol3' package can be used to perform calculations using a general density function method. When the optimal molecular structure is determined using the above-described method, an energy level occupied by electrons can be obtained as a result. HOMO energy refers to the orbital energy of the highest energy level among the molecular orbitals filled with electrons when the neutral energy is obtained, and LUMO energy corresponds to the orbital energy of the lowest energy level among the molecular orbitals without electrons.

* HOMO/LUMO calculation

Experimentally, the HOMO energy level uses the IP (Ionization Potential) value (Equation-1 below) measured using a UPS (ultraviolet photoemission spectroscopy), and the LUMO energy level is generally an optical gap from the HOMO energy level. The value minus (Equation-2 below) is used.

[Equation-1]

HOMO = IP (Ionization Potential)

[Equation-2]

LUMO = IP-Optical Gap

Computatively, the HOMO and LUMO in the theoretical neutral state, along with the actual measured values in the experiment, are provided in the following two ways.

Method 1) How to use IP and Optical Gap

According to the method obtained in the experiment, the IP and optical gap of the X molecule are obtained using the following equations-3 and 4.

[Equation-3]

IP (Ionization potential) = E ^X+ _cation -E ^x _neutral

[Equation-4]

Optical Gap = E ^S1 _S0 -E ^S0 _S0

In the above formula-3 '

'Means energy whose charge is 0, X ⁺ , or X ^- in a structure whose geometry is optimized to be cation, anion, or neutral. That is, electron affinity means the difference between the safest energy of the anion and the safest energy of the neutral structure, and may mean the energy emitted when adding one electron in the neutral state.

In Equation 4, S0 is a single term of the ground state, S1 is a single term of the first excited state, and E ^S1 _S0 is a single term energy of the ground state and a single term of the first excited state. The term energy difference means, and E ^S0 _S0 means the energy difference inside the single term in the ground state. At this time, E ^S0 _S0 means the energy difference due to the change in the geometry inside the single term in the ground state. In addition, under the assumption that the structural changes of S0 and S1 are not large, the energy and fluorescence values of absorption are similar. Accordingly, Opctical Gap corresponds to the S0-S1 gap. The base and excitation energy is based on values obtained using a pan density function.

Method 2) Method using solid state IP and Optical Gap

When implemented as a layer, since it becomes a solid state rather than a single molecule, the effect at that time is corrected as shown in Equation 5 below considering the molecular shape and the like to HOMO calc. A value can be obtained, and the LUMO energy level is obtained by substituting this value into the IP value of Equation 2 above. However, transition metal cannot be calculated.

[Equation-5]

HOMO calc. = IP + △ (solid / molecule)

In the above equation-5, △ (solid / molecule) means the energy difference between the monomolecular state (solid state) and the solid state (solid state), asphericity (Asphericity), radius of rotation (Radius of gyration), molecular weight (Molecular weight) and so on.

The organic light emitting device according to the present specification includes a first electrode; A second electrode; And at least one organic material layer provided between the first electrode and the second electrode, and at least one layer of the organic material layer comprises a compound represented by Formula 1 described above.

The organic light-emitting device of the present specification may be manufactured by a conventional method and material for manufacturing an organic light-emitting device, except that one or more organic material layers are formed using the compound represented by Chemical Formula 1 above.

The organic material layer including the compound represented by Chemical Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution 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 specification may have a single layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present specification is a hole injection layer, a hole transport layer, a layer that simultaneously performs hole transport and hole injection as an organic material layer, an electron suppressing layer, a light emitting layer, an electron transport layer, an electron injection layer, a layer that simultaneously performs electron transport and electron injection It may have a structure including a. However, the structure of the organic light emitting device is not limited to this, and may include fewer or more organic material layers.

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

In the organic light emitting device of the present specification, the organic material layer 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 Formula 1 described above.

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

According to another exemplary embodiment, the organic material layer includes a light emitting layer, the light emitting layer includes the compound represented by Formula 1 as a dopant in the light emitting layer, and the maximum emission wavelength of the dopant is 430 nm to 470 nm. The compound of the present invention has the maximum emission wavelength in the above range as it contains two amine groups, but the compound containing one amine group has the maximum emission wavelength in the range of about 410 nm to 430 nm.

The emission layer may further include a host having a maximum emission wavelength of 400 nm to 440 nm, and the compound of the present invention including two amine groups has excellent efficiency due to easy energy transfer in relation to the host. The compound containing one amine group does not smoothly transfer energy in relation to the host, so the efficiency of the device is deteriorated. The maximum emission wavelength is 1x10 ^-5 in the toluene solution After diluting with M/L, it can be measured at room temperature. The maximum emission peak of the compound was measured using FP-8600 from JASCO, and the emission spectrum at an excitation wavelength of 300 nm was 430 nm to 470 nm, and HPLC grade anhydrous toluene was used as a solvent.

According to the exemplary embodiment of the present specification, the compound represented by Chemical Formula 1 is included in the light emitting layer of the organic light emitting device as a blue dopant.

According to another exemplary embodiment, the compound represented by Chemical Formula 1 is included in a light emitting layer of an organic light emitting device as a fluorescent dopant for a thermally activated delayed fluorescence (TADF) device. At this time, the compound emits a heat-activated delayed fluorescent light in the light emitting layer. The thermally activated delayed fluorescence emission reverses the transition between the triplet excited state and the singlet excited state, and the exciton of the singlet excited state moves to the ground state. It means to cause fluorescence, and it is possible to obtain a high efficiency organic light emitting device.

According to an exemplary embodiment of the present invention, the compound represented by Chemical Formula 1 may be included as a dopant in the light emitting layer, and may further include a host such as an anthracene-based compound having the following structure, but is not limited thereto.

In another exemplary embodiment, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Formula 1 as a dopant in the light emitting layer, a fluorescent host or a phosphorescent host, and other organic compounds, metals, or Metal compounds may be included as dopants.

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

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 Formula 1 as a host of the light emitting layer.

As another example, the organic material layer may include a light emitting layer, and the light emitting layer may include a compound represented by Chemical Formula 1 as a host of the light emitting layer, and further include a dopant.

The light emitting layer includes a host and a dopant, and the content of the dopant may include 1 part by weight to 20 parts by weight, and more preferably 1 part by weight to 5 parts by weight based on 100 parts by weight of the host.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

1 illustrates a structure of an organic electronic 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 represented by Chemical Formula 1 may be included in the light emitting layer 3.

In FIG. 2, 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 the substrate 1 in an organic light emitting device. The structure is illustrated. In such a structure, the compound represented by Chemical Formula 1 may be included in one or more of the hole injection layer 5, the hole transport layer 6, the light emitting layer 7, and the electron transport layer 8.

For example, the organic light emitting device according to the present specification 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 To form an anode, to form an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron suppressing layer, an electron transport layer, and an electron injection layer, and then depositing a material that can be used as a cathode thereon Can be. In addition to this method, an organic electronic device may be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.

The organic layer includes a hole injection layer, a hole transport layer, an electron injection and electron transport layer simultaneously, an electron suppression layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron injection and electron transport layer simultaneously, a hole suppression layer, etc. It may be a multi-layer structure, but is not limited thereto, and may be a single-layer structure. In addition, the organic material layer has a smaller number of solvent processes, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer, rather than deposition using various polymer materials. Can be prepared in layers.

Each layer constituting the organic light emitting device described below may be formed of one layer or two or more layers, and the layers of two or more layers may be made of the same material or different materials.

The positive electrode is an electrode for injecting holes, and a positive electrode material is preferably a material having a large work function to facilitate hole injection into an 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 is an electrode for injecting electrons, and the cathode material is preferably a material having a small work function to facilitate electron injection into an 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 injection layer is a layer that serves to smoothly inject holes from the anode to the light emitting layer. As a hole injection material, a hole injection material is a material that can be easily injected with holes from the anode at a low voltage, and HOMO (highest occupied) of the hole injection material It is preferable that the molecular orbital is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based substances. Organic materials, anthraquinones, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

The hole transport layer may serve to facilitate the transport of holes. As a hole transport material, a material that can receive holes from the anode or the hole injection layer and transfer them to the light emitting layer is suitable for 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.

An electron suppressing layer may be provided between the hole transport layer and the light emitting layer. The electron suppressing layer may be a material known in the art.

The emission layer may emit red, green, or blue, 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 transporting and combining holes and electrons from the hole transport layer and the electron transport layer, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole compounds; Poly(p-phenylenevinylene) (PPV)-based 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.

When the light-emitting layer emits red light, PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium are used as the light emitting dopant. ), phosphorescent materials such as octaethylporphyrin platinum (PtOEP), and fluorescent materials such as Alq ₃ (tris(8-hydroxyquinolino)aluminum) may be used, but are not limited thereto. When the light emitting layer emits green light, a phosphorescent material such as Ir(ppy) ₃ (fac tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq3(tris(8-hydroxyquinolino)aluminum) can be used as the light emitting dopant. However, it is not limited to this. When the light emitting layer emits blue light, a phosphorescent material such as (4,6-F2ppy) ₂ Irpic is used as a light emitting dopant, but spiro-DPVBi, spiro-6P, distylbenzene (DSB), distriarylene (DSA), Fluorescent materials such as PFO-based polymers and PPV-based polymers may be used, but are not limited thereto.

A hole suppressing layer may be provided between the electron transport layer and the light emitting layer, and materials known in the art may be used.

The electron transport layer may serve to facilitate the transport of electrons. As the electron transporting material, a material capable of receiving electrons well from the cathode 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 injection layer may serve to facilitate injection of electrons. As an electron injection material, it has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect for the light emitting layer or light emitting material, prevents movement of excitons generated in the light emitting layer to the hole injection layer, and also , A compound having excellent thin film forming ability is preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and their derivatives, 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, 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)( There are o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, It is not limited to this.

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

<< 합성예Synthetic example >>

합성예Synthetic example 1. One.

[Intermediate E-3] [Intermediate 1] [Compound 1]

The intermediate E-3 (13.4 g, 15.0 mmol) and the intermediate 1 (6.8 g, 30.1 mmol) were added to xylene (200 mL). After adding NatBuO (4.3 g) and bis(tri-tert-butylphosphine) palladium [BTP] (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the produced solid was recrystallized from ethyl acetate three times to prepare Compound 1. (4.7 g, yield 42%, MS:[M+H] ⁺ =744)

합성예Synthetic example 2. 2.

[Intermediate E-3] [Intermediate 2] [Compound 2]

The intermediate E-3 (13.4 g, 15.0 mmol) and the intermediate 2 (8.5 g, 30.1 mmol) were added to xylene (200 mL). After adding NatBuO (4.3 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the solid produced by filtration was recrystallized from ethyl acetate three times to prepare Compound 2. (6.4 g, yield 50%, MS:[M+H] ⁺ =856)

합성예Synthetic example 3. 3.

[Intermediate E-4] [Intermediate 3] [Compound 3]

The intermediate E-4 (14.2 g, 15.0 mmol) and the intermediate 3 (8.6 g, 30.1 mmol) were added to xylene (200 mL). After adding NatBuO (4.3 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the produced solid was recrystallized from ethyl acetate three times to prepare the compound 3. (7.0 g, yield 51%, MS:[M+H] ⁺ =920)

합성예Synthetic example 4. 4.

[Intermediate E-3] [Intermediate 4] [Compound 4]

The intermediate E-3 (13.4 g, 15.0 mmol) and the intermediate 4 (8.7 g, 30.1 mmol) were added to xylene (200 mL). After adding NatBuO (4.3 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was recrystallized from ethyl acetate three times to prepare the compound 4. (7.2 g, yield 55%, MS:[M+H] ⁺ =874)

합성예Synthetic example 5. 5.

[Intermediate E-1] [Intermediate 5] [Compound 5]

The intermediate E-1 (15.0 g, 17.2 mmol) and the intermediate 5 (6.4 g, 34.3 mmol) were added to xylene (200 mL). After adding NatBuO (5.0 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the produced solid was recrystallized from ethyl acetate three times to prepare the compound 5. (5.9 g, yield 50%, MS: [M+H] ⁺ = 681)

합성예Synthetic example 6. 6.

[Intermediate E-2] [Intermediate 6] [Compound 6]

The intermediate E-2 (15.0 g, 15.0 mmol) and the intermediate 6 (5.8 g, 30.1 mmol) were added to xylene (200 mL). After adding NatBuO (4.3 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was recrystallized from ethyl acetate three times to prepare Compound 6. (7.1 g, yield 58%, MS:[M+H] ⁺ =818)

In the above synthesis example, the synthesis process of compounds 1 to 6 is exemplified, but intermediates in which various kinds of substituents are bonded are synthesized through reactions known in the art, or commercially available intermediates are used to synthesize compounds 1 to 6 and the like. Compounds can be synthesized.

<< 실험예Experimental Example 1> 1>

Table 1 shows the simulation result values of Compound 1, Compound 1-1, Comparative Compound 1 and Comparative Compound 2 measured under the following apparatus and conditions. From the results of Table 4 below, Compound 1 and Compound 1-1 have appropriate values for band gap energy to be used as a blue dopant in the light emitting layer, but Comparative Compounds 1 and 2 in which the band gap energy exceeds 2.9 eV. The emission wavelength range is not suitable for use as a blue dopant, so it can be predicted that the luminous efficiency is very low.

DFT calculation: BPW91/DND (DMol3)

Geometry optimization: Single point energy calculation

UV calculation: ZINDO (G03)

Band gap calculation: TD (G03)

Solid state IP calculation: QSPR (Adriana)

화합물compound	HOMO (eV)HOMO (eV)	LUMO(eV)LUMO (eV)	Band gapBand gap
<화합물 1> <Compound 1>	5.435.43	2.672.67	2.762.76
<화합물 1-1> <Compound 1-1>	5.445.44	2.662.66	2.782.78
<비교 화합물 1> <Comparative Compound 1>	5.565.56	2.642.64	2.922.92
<비교 화합물 2> <Comparative Compound 2>	5.615.61	2.692.69	2.922.92

<실험예 2><Experimental Example 2>

실시예 1.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 used by Millipore Co. Distilled water, which was second filtered as a product filter, was used. After washing the ITO for 30 minutes, ultrasonic washing was repeated for 10 minutes by repeating it twice with distilled water. After washing with distilled water, ultrasonic cleaning was performed in the order of isopropyl alcohol, acetone, and methanol, followed by drying.

On the ITO transparent electrode thus prepared, the following HAT was thermally vacuum-deposited to a thickness of 50 Pa to form a hole injection layer. The following HT-A 1000 진공 was vacuum-deposited as a hole transport layer, and the following HT-B 100 Å was deposited. The following compound 1 was doped with 4 wt% as a dopant in the following H-A as a host as a light emitting layer and vacuum-deposited to a thickness of 200 Pa. Then, 300 Å of the following ET-A and the following Liq were deposited in a 1:1 ratio, and then 150 µm thick silver (Ag) was doped with 10 wt% magnesium (Mg), and 1,000 µm thick aluminum was deposited. An anode was formed to manufacture an organic light emitting device.

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.

Compound 1 Compound 2

Compound 3 Compound 4

Compound 5 Compound 6

Compound 7

실시예Example 2 내지 21 및 2 to 21 and 비교예Comparative example 1 내지 9 1 to 9

In Example 1, except for using the compounds shown in Tables 1 to 3 in place of the HA as the host of the light emitting layer, and using the compounds shown in Tables 1 to 3 in place of the compound 1 as a dopant in the Example 1 and Similarly, an organic light emitting device was manufactured.

The driving voltage and luminous efficiency of the organic light-emitting devices of Examples 1 to 21 and Comparative Examples 1 to 9 were measured at a current density of 10 mA/cm ² , and the time to be 95% compared to the initial luminance at a current density of 20 mA/cm ² . (LT95) was measured. The results are shown in Tables 1 to 3 below.

	호스트Host	도펀트Dopant	@ 10 mA/cm² @ 10 mA/cm ²			LT95LT95
	호스트Host	도펀트Dopant	전압(V)Voltage (V)	효율(cd/A)Efficiency (cd/A)	colorcolor	수명(hr)Life (hr)
실시예 1Example 1	H-A H-A		화합물 1Compound 1	4.224.22	7.287.28	blueblue	130130
실시예 2Example 2	H-A H-A		화합물 2Compound 2	4.214.21	6.846.84	blueblue	130130
실시예 3Example 3	H-A H-A		화합물 3Compound 3	4.324.32	6.966.96	blueblue	125125
실시예 4Example 4	H-A H-A		화합물 4Compound 4	4.324.32	6.616.61	blueblue	125125
실시예 5Example 5	H-AH-A	화합물 5Compound 5	4.304.30	6.516.51	blueblue	110110
실시예 6Example 6	H-A H-A		화합물 6Compound 6	4.204.20	6.666.66	blueblue	115115
실시예 7Example 7	H-A H-A		화합물 7Compound 7	4.204.20	6.896.89	blueblue	110110
비교예 1Comparative Example 1	H-AH-A	D-1D-1	4.394.39	5.135.13	blueblue	7575
비교예 2Comparative Example 2	H-AH-A	D-2D-2	4.424.42	3.503.50	blueblue	5050
비교예 3Comparative Example 3	H-AH-A	D-3D-3	4.404.40	4.884.88	blueblue	8585

	호스트Host	도펀트Dopant	@ 10 mA/cm² @ 10 mA/cm ²			LT95LT95
	호스트Host	도펀트Dopant	전압(V)Voltage (V)	효율(cd/A)Efficiency (cd/A)	colorcolor	수명(hr)Life (hr)
실시예 8Example 8	H-B H-B		화합물 1Compound 1	4.354.35	7.217.21	blueblue	120120
실시예 9Example 9	H-B H-B		화합물 2Compound 2	4.344.34	6.776.77	blueblue	140140
실시예 10Example 10	H-B H-B		화합물 3Compound 3	4.454.45	6.896.89	blueblue	135135
실시예 11Example 11	H-B H-B		화합물 4Compound 4	4.454.45	6.546.54	blueblue	125125
실시예 12Example 12	H-BH-B	화합물 5Compound 5	4.434.43	6.446.44	blueblue	115115
실시예 13Example 13	H-B H-B		화합물 6Compound 6	4.314.31	6.796.79	blueblue	115115
실시예 14Example 14	H-B H-B		화합물 7Compound 7	4.314.31	6.826.82	blueblue	135135
비교예 4Comparative Example 4	H-BH-B	D-4D-4	4.564.56	5.125.12	blueblue	8080
비교예 5Comparative Example 5	H-BH-B	D-5D-5	4.544.54	4.504.50	blueblue	6060
비교예 6Comparative Example 6	H-BH-B	D-6D-6	4.554.55	5.325.32	blueblue	9595

	호스트Host	도펀트Dopant	@ 10 mA/cm² @ 10 mA/cm ²			LT95LT95
	호스트Host	도펀트Dopant	전압(V)Voltage (V)	효율(cd/A)Efficiency (cd/A)	colorcolor	수명(hr)Life (hr)
실시예 15Example 15	H-C H-C		화합물 1Compound 1	4.064.06	7.017.01	blueblue	125125
실시예 16Example 16	H-C H-C		화합물 2Compound 2	4.124.12	6.466.46	blueblue	115115
실시예 17Example 17	H-C H-C		화합물 3Compound 3	4.214.21	6.996.99	blueblue	130130
실시예 18Example 18	H-C H-C		화합물 4Compound 4	4.054.05	6.826.82	blueblue	125125
실시예 19Example 19	H-CH-C	화합물 5Compound 5	4.004.00	6.136.13	blueblue	105105
실시예 20Example 20	H-C H-C		화합물 6Compound 6	4.084.08	6.226.22	blueblue	115115
실시예 21Example 21	H-C H-C		화합물 7Compound 7	4.104.10	6.096.09	blueblue	120120
비교예 7Comparative Example 7	H-CH-C	D-1D-1	4.324.32	5.105.10	blueblue	7070
비교예 8Comparative Example 8	H-CH-C	D-2D-2	4.334.33	4.504.50	blueblue	5050
비교예 9Comparative Example 9	H-CH-C	D-7D-7	4.404.40	6.006.00	blueblue	100100

From Tables 1 to 3, it can be seen that Examples 1 to 21 of the present application have lower driving voltages of devices than Comparative Examples 1 to 9, and are very excellent in efficiency and life.

Specifically, Comparative Examples 1 and 3 to 7 are compounds D-1 and D-, in which pyrene, naphthobenzofuran, fluorene, dibenzofluorene, or dinaphthofuran are bonded between two amine groups, respectively. 3, Compound D-4, Compound D-5 or Compound D-6 is used as a dopant in the light emitting layer, but it can be confirmed that performance is lower than that of the device using the compound of the present application.

Comparative Examples 2 and 8 are those using a compound D-2 having a different bonding position between the compound of the present invention and an amine group, and it can be confirmed that performance of the device is lower than that of the device using the compound of the present invention, and in particular, the life of the device is very low.

In addition, Comparative Example 9 is the same as the compound of the present invention and the core structure and the binding position of the amine group, but using a compound D-7 in which no further substituents other than the amine group are bonded to the core structure of dinaphthofuran, a device using the compound of the present invention It can be seen that the driving voltage is higher, and the efficiency and life are lower.

Claims

Compound represented by the formula (1):

[Formula 1]

In Chemical Formula 1,

X is O, S or Si,

Ar 1 to Ar 4 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 cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group; Or combine with adjacent groups to form a substituted or unsubstituted carbazole,

R 1 to R 8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, at least one of R 1 to R 8 is deuterium; Halogen group; Cyano group; Nitro group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
The method according to claim 1,

The -N(Ar 1 )(Ar 2 ) and -N(Ar 3 )(Ar 4 ) are the same as or different from each other, and each independently a compound represented by Formula 1-A or 1-B:

[Formula 1-A]

[Formula 1-B]

In Chemical Formulas 1-A and 1-B,

R 11 and 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 cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R 20 to R 27 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

In the above structures,
Means the position to be joined.
The method according to claim 1,

The Ar 1 to Ar 4 are the same as or different from each other, and each independently substituted or unsubstituted ethyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted benzofluorenyl group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted carbazole group; Or Formula A: Or a compound that combines with adjacent groups to form a substituted or unsubstituted carbazole:

[Formula A]

In Chemical Formula A,

R 30 is hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

n1 is an integer from 0 to 7, and when n1 is 2 or more, 2 or more R 30 are the same as or different from each other,

Means the position to be joined.
The method according to claim 1,

Formula 1 is a compound represented by the following Formula 1-1 or 1-2:

[Formula 1-1]

[Formula 1-2]

In Chemical Formulas 1-1 and 1-2,

The definitions of X, R 1 to R 8 , and Ar 1 to Ar 3 are the same as those in Formula 1,

R 30 and R 30 ′ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

n1 and n1' are each an integer of 0 to 7, and when n1 and n1' are each 2 or more, structures in two or more parentheses are the same or different from each other.
The method according to claim 1,

The Ar 1 to Ar 4 are the same as or different from each other, and each independently an alkyl group having 1 to 10 carbon atoms, and a compound selected from the following structures, or combined with an adjacent group to form a substituted or unsubstituted carbazole:

In the above structures,

W is O, S or NR 103 ,

R 101 to R 103 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,

The structures are deuterium; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; And one or more substituents selected from the group consisting of substituted or unsubstituted aryl groups,

In the above structures,
Means the position to be joined.
The method according to claim 1,

The -N(Ar 1 )(Ar 2 ) and -N(Ar 3 )(Ar 4 ) are the same as or different from each other, and each independently a compound represented by any one of the following structures:

In the above structures,
Means the position to be joined.
The method according to claim 1,

The compound represented by Formula 1 is a compound represented by any one of the following compounds:

.
A first electrode; A second electrode; And at least one layer of an organic material provided between the first electrode and the second electrode, and at least one layer of the organic material layer comprises a compound according to any one of claims 1 to 7.
The method according to claim 8,

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 8,

The organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or electron injection layer includes the compound.
The method according to claim 8,

The organic material layer includes an emission layer, and the emission layer includes the compound.
The method according to claim 8,

The organic material layer includes a light emitting layer, the light emitting layer comprises the compound as a dopant of the light emitting layer, the maximum emission wavelength of the dopant is an organic light emitting device of 430nm to 470nm.
The method according to claim 12,

The emission layer further comprises an organic light emitting device having a host having a maximum emission wavelength of 400 nm to 440 nm.