KR20190106761A - Multicyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification provides a compound of chemical formula 1 and an organic light emitting device comprising the same. The compound described in the present specification can be used as a material of an organic material layer of the organic light emitting device. When manufacturing the organic light emitting device comprising the compound according to at least one embodiment, it is possible to obtain the organic light emitting device having high efficiency and long lifespan.

Description

Polycyclic compound and organic light emitting device including the same {MULTICYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME}

This specification claims the benefit of the Korean Patent Application No. 10-2018-0026429 filed on March 6, 2018 to the Korean Intellectual Property Office, the contents of which are incorporated herein in its entirety.

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

In the present specification, an organic light emitting device is a light emitting device using an organic semiconductor material, and requires an exchange of holes and / or electrons between an electrode and the organic semiconductor material. The organic light emitting device can be classified into two types according to the operation principle. First, an exciton is formed in the organic layer by photons introduced into the device from an external light source, and the exciton is separated into electrons and holes, and these electrons and holes are transferred to different electrodes to be used as current sources (voltage sources). It is a light emitting element of the form. The second is a light emitting device in which holes and / or electrons are injected into the organic semiconductor material layer that interfaces with the electrodes by applying voltage or current to two or more electrodes, and is operated by the injected electrons and holes.

In general, organic light emitting phenomenon refers to a phenomenon of converting 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, a cathode, and an organic material layer therebetween. The organic material layer is often made of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer. When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer, and excitons are formed when the injected holes and the electrons meet each other. When it falls back to the ground, it glows. Such organic light emitting devices are known to have characteristics such as self-luminous, high brightness, high efficiency, low driving voltage, wide viewing angle, and high contrast.

Materials used as the organic material layer in the organic light emitting device may be classified into light emitting materials and charge transport materials such as hole injection materials, hole transport materials, electron transport materials, electron injection materials and the like depending on their functions. The luminescent material includes blue, green, and red luminescent materials and yellow and orange luminescent materials necessary to realize better natural colors depending on the emission color.

In addition, a host / dopant system may be used as the light emitting material in order to increase the light emission efficiency through increase in color purity and energy transfer. The principle is that when a small amount of dopant having a smaller energy band gap and excellent luminous efficiency than the host mainly constituting the light emitting layer is mixed in the light emitting layer, excitons generated in the host are transported to the dopant to give high efficiency light. At this time, since the wavelength of the host shifts to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.

In order to fully exhibit the excellent characteristics of the above-described organic light emitting device, a material forming the organic material layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc., is supported by a stable and efficient material. The development of new materials continues to be required.

International Patent Publication No. 2017-086320

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

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

[Formula 1]

In Chemical Formula 1,

A is a substituted or unsubstituted benzene ring,

X ₁ and X ₂ are the same as or different from each other, and are each independently O, S, or N (Ra),

Ra, R ₁ and R ₂ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl groups; Boron group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

B ₁ to B ₈ are the same as or different from each other, and each independently N, C (Rb) or C (Rb '),

Rb is hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl groups; Boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

Rb 'is a substituted or unsubstituted amine group; Or a heterocyclic group containing one or more substituted or unsubstituted N,

At least one of B ₁ to B ₄ is C (Rb '), at least one of B ₅ to B ₈ is C (Rb'),

n1 is an integer of 0 to 2, when n1 is 2, R1 is the same as or different from each other,

n2 is an integer of 0 to 2, and when n2 is 2, R2 is the same as or different from each other.

In addition, the present invention is a first electrode; A second electrode provided to face the first electrode; And an organic light emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound described above.

The compound described herein can be used as the material of the organic material layer of the organic light emitting device. When manufacturing an organic light emitting device including the compound according to at least one embodiment, it is possible to obtain an organic light emitting device having a high efficiency and a long life, when the compound of the present invention is included in the light emitting layer of the organic light emitting device, high color reproducibility It is possible to manufacture an organic light emitting device having a.

FIG. 1 shows an example of an organic light emitting element composed of 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 element consisting of 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.
3 is a diagram showing an MS graph of Compound BD-A.
4 is a diagram showing an MS graph of Compound BD-B.
5 is a diagram showing an MS graph of Compound BD-C.
6 is a diagram showing an MS graph of Compound BD-D.
7 is a diagram showing an MS graph of Compound BD-E.

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

The present specification provides a compound represented by the following Formula 1. When the compound represented by the following formula (1) is used in the organic material layer of the organic light emitting device, the efficiency, color reproducibility, and lifespan characteristics of the organic light emitting device are always maintained.

Compounds having the same core structure as the compound represented by the following Chemical Formula 1, but not including one or more of B ₁ to B ₄ and one or more of B ₅ to B ₈ that contain an amine group or N or one or more heterocyclic groups are organic. When applied as a light emitting layer dopant of the light emitting device, there is a problem that the light emission intensity is weak, and the quantum efficiency is weak.

[Formula 1]

In Chemical Formula 1,

A is a substituted or unsubstituted benzene ring,

X ₁ and X ₂ are the same as or different from each other, and are each independently O, S, or N (Ra),

Ra, R ₁ and R ₂ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl groups; Boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

B ₁ to B ₈ are the same as or different from each other, and each independently N, C (Rb) or C (Rb '),

Rb is hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl groups; Boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

Rb 'is a substituted or unsubstituted amine group; Or a heterocyclic group containing one or more substituted or unsubstituted N,

At least one of B ₁ to B ₄ is C (Rb '), at least one of B ₅ to B ₈ is C (Rb'),

n1 is an integer of 0 to 2, when n1 is 2, R1 is the same as or different from each other,

n2 is an integer of 0 to 2, and when n2 is 2, R2 is the same as or different from each other.

In the present specification, when a part "includes" a certain component, this means that it may further include other components, without excluding other components unless specifically stated otherwise.

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

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

The term "substituted" means that a hydrogen atom bonded to a 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 replaced, that is, a position where the substituent can be substituted, if two or more are substituted , Two or more substituents may be the same or different from each other.

As used herein, the term "substituted or unsubstituted" is deuterium (-D); Halogen group; Cyano group (-CN); Silyl groups; Boron group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group, or two or more of the substituents exemplified above are substituted with a substituent, or means that do not have any substituents. For example, "a substituent to which two or more substituents are linked" 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 linked.

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 a chemical formula of -SiY ₁ Y ₂ Y ₃ , wherein Y ₁ , Y ₂ and Y ₃ are each hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group. Specific examples of the silyl group include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, and phenylsilyl group. Do not.

In the present specification, the boron group may be represented by a chemical formula of -BY ₄ Y ₅ , wherein Y ₄ and Y ₅ are each hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group. The boron group may include, but is not limited to, trimethylboron group, triethylboron group, t-butyldimethylboron group, triphenylboron group, and phenylboron group.

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

In the present specification, the alkenyl group may be linear or branched chain, the carbon number is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl (ethenyl), 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, and the like. It is not limited to these.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one 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 and the like, but is not limited thereto.

In the present specification, the amine group is -NH ₂ ; Alkylamine group; Arylalkylamine group; Arylamine group; Aryl heteroaryl amine group; Alkylheteroarylamine group It can be selected from the group consisting of a cycloalkylarylamine group and a heteroarylamine group, and carbon number is not particularly limited, but is preferably 1 to 60.

In the present specification, the alkylamine group is not particularly limited, but may be 1 to 40, according to one embodiment may be 1 to 20. Specific examples of the alkylamine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, and the like, but are not limited thereto.

In the present specification, a cycloalkylarylamine group means an amine group substituted with a cycloalkyl group and an aryl group.

In the 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, may be a polycyclic aryl group. The arylamine group including two or more aryl groups may simultaneously include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group.

Specific examples of the arylamine group include phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, diphenylamine group, phenylnaphthylamine group, biphenylphenylamine group, dibiphenylamine group, and fluorine. And a phenylphenyl group, but are not limited thereto.

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 heteroaryl group, may be a polycyclic heteroaryl group. The heteroarylamine group including two or more heteroaryl groups may simultaneously include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group.

In the present specification, the arylalkylamine group means an amine group substituted with an aryl group and an alkyl group.

In the present specification, the arylheteroarylamine group means an amine group substituted with an aryl group and a heteroaryl group.

In the present specification, the arylalkylamine group means an amine group substituted with an aryl group and an alkyl group.

In the present specification, an alkylheteroarylamine group means an amine group substituted with an alkyl group and a heteroaryl group.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group, but may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, peryllenyl 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 be bonded to each other to form a spiro structure.

,

등의 스피로플루오레닐기,

(9,9-디메틸플루오레닐기), 및

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

,

Spirofluorenyl groups, such as

(9,9-dimethylfluorenyl group), and

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

In the present specification, the heterocyclic group is a ring group containing one or more of N, O, P, S, Si, and Se as hetero atoms, 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, for example, pyridine group, pyrrole group, pyrimidine group, pyridazinyl group, furan group, thiophene group, imidazole group, pyrazole group, dibenzofuran group, dibenzothiophene group, carbazole group , Indolocarbazole groups, naphthobenzofuran groups and the like, but are not limited thereto.

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

In the present specification, in the substituted or unsubstituted heterocycle formed by bonding of adjacent groups (Ar ₁ and Ar ₂ of Formula A herein), the description of the heterocyclic group may be applied except that the heterocycle is divalent. have.

In the present specification, the description of the aryl group described above may be applied except that the arylene group is a divalent group.

In the present specification, the description about the heteroaryl group described above may be applied except that the heteroarylene group is a divalent group.

According to an exemplary embodiment of the present specification, A is a substituted or unsubstituted benzene ring.

A is hydrogen, deuterium, halogen, cyano group (-CN), silyl group, substituted or unsubstituted alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted aryl group and substituted or unsubstituted heteroaryl Or a benzene ring unsubstituted or substituted with one or more selected from the group consisting of groups.

According to an embodiment of the present invention, A is hydrogen, deuterium, halogen, cyano group (-CN), silyl group, substituted or unsubstituted C1-20 alkyl group, substituted or unsubstituted C2-20 It is a benzene ring unsubstituted or substituted with one or more selected from the group consisting of an alkenyl group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

According to another example, A is hydrogen, deuterium, halogen, cyano group (-CN), silyl group, substituted or unsubstituted methyl group, substituted or unsubstituted ethyl group, substituted or unsubstituted propyl group, Or a substituted or unsubstituted benzene ring selected from the group consisting of a substituted or unsubstituted butyl group, a substituted or unsubstituted ethenyl group, a substituted or unsubstituted phenyl group, and a substituted or unsubstituted pyrimidine group.

According to another example, A is hydrogen, deuterium, halogen, cyano (-CN), trimethylsilyl, methyl, ethyl, propyl, butyl, methylethenyl, trifluorophenyl, butyl It is a benzene ring unsubstituted or substituted with one or more selected from the group consisting of a phenyl group substituted or unsubstituted with a group and a pyrimidine group substituted with a phenyl group.

According to an embodiment of the present invention, Chemical Formula 1 may be represented by any one of the following Chemical Formulas 2 to 4.

[Formula 2]

[Formula 3]

[Formula 4]

In Chemical Formulas 2 to 4,

X ₁ and X ₂ are the same as or different from each other, and each independently O, S Or N (Ra),

Z ₁ to Z ₆ , Ra, R ₁ and R ₂ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl groups; Boron group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

B ₁ to B ₈ are the same as or different from each other, and each independently N, C (Rb) or C (Rb '),

Rb is hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl groups; Boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

Rb 'is a substituted or unsubstituted amine group; Or a heterocyclic group containing one or more substituted or unsubstituted N,

At least one of B ₁ to B ₄ is C (Rb '), at least one of B ₅ to B ₈ is C (Rb'),

n1 is an integer of 0 to 2, when n1 is 2, R1 is the same as or different from each other,

n2 is an integer of 0 to 2, and when n2 is 2, R2 is the same as or different from each other.

In one embodiment of the present invention, Z ₁ to Z ₆ are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group (-CN), silyl group, substituted or unsubstituted alkyl group, substituted or Unsubstituted alkenyl group, substituted or unsubstituted aryl group, or substituted or unsubstituted heteroaryl group.

According to an embodiment of the present invention, Z ₁ to Z ₆ are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group (-CN), a silyl group, a substituted or unsubstituted carbon number 1 to 20 An alkyl group, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

According to another example, Z ₁ to Z ₆ are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group (-CN), silyl group, substituted or unsubstituted methyl group, substituted or unsubstituted A substituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted ethenyl group, a substituted or unsubstituted phenyl group or a substituted or unsubstituted pyrimidine group.

According to another example, Z ₁ to Z ₆ are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group (-CN), trimethylsilyl group, methyl group, ethyl group, propyl group, butyl group , A methylethenyl group, a trifluorophenyl group, a phenyl group unsubstituted or substituted with a butyl group, or a pyrimidine group substituted with a phenyl group.

According to an embodiment of the present invention, Chemical Formula 1 may be represented by any one of the following Chemical Formulas 1-1 to 1-6.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

In Chemical Formulas 1-1 to 1-6,

X ₁ and X ₂ are the same as or different from each other, and each independently O, S Or N (Ra),

Z ₂₁ to Z ₃₂ , Ra, R ₁ and R ₂ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); Silyl groups; Boron group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

B ₁ to B ₈ are the same as or different from each other, and each independently N, C (Rb) or C (Rb '),

Rb is hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); Silyl groups; Boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

Rb 'is a substituted or unsubstituted amine group; Or a heterocyclic group containing one or more substituted or unsubstituted N,

At least one of B ₁ to B ₄ is C (Rb '), at least one of B ₅ to B ₈ is C (Rb'),

n1 is an integer of 0 to 2, when n1 is 2, R1 is the same as or different from each other,

n2 is an integer of 0 to 2, and when n2 is 2, R2 is the same as or different from each other.

In one embodiment of the present invention, Z ₂₁ to Z ₃₂ are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group (-CN), a silyl group, a substituted or unsubstituted alkyl group, a substituted or Unsubstituted alkenyl group, substituted or unsubstituted aryl group, or substituted or unsubstituted heteroaryl group.

According to an embodiment of the present invention, Z ₂₁ to Z ₃₂ are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group (-CN), a silyl group, a substituted or unsubstituted carbon number 1 to 20 An alkyl group, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

According to another example, Z ₂₁ to Z ₃₂ are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group (-CN), silyl group, substituted or unsubstituted methyl group, substituted or unsubstituted A substituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, a substituted or unsubstituted ethenyl group, a substituted or unsubstituted phenyl group or a substituted or unsubstituted pyrimidine group.

According to another example, Z ₂₁ to Z ₃₂ are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group (-CN), trimethylsilyl group, a methyl group, an ethyl group, a propyl group, a butyl group , A methylethenyl group, a trifluorophenyl group, a phenyl group unsubstituted or substituted with a butyl group, or a pyrimidine group substituted with a phenyl group.

According to one embodiment of the present invention, X ₁ and X ₂ are the same as or different from each other, and each independently O, S, S (= O), SO ₂ or N (Ra).

According to another example, X ₁ and X ₂ are O.

According to another example, X ₁ and X ₂ are S.

According to another example, X ₁ and X ₂ are N (Ra).

According to another example, one of X ₁ and X ₂ is O and the other is S.

According to another example, one of X ₁ and X ₂ is O and the other is N (Ra).

According to another example, one of X ₁ and X ₂ is S and the other is N (Ra).

Ra is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.

According to another example, 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 or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In another example, Ra is hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

According to another example, Ra is hydrogen; heavy hydrogen; An aryl group having 6 to 30 carbon atoms unsubstituted or substituted with a halogen group or an alkyl group having 1 to 20 carbon atoms; Or a heteroaryl group having 2 to 30 carbon atoms unsubstituted or substituted with a halogen group or an alkyl group having 1 to 20 carbon atoms.

In another example, Ra is hydrogen; heavy hydrogen; Substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted carbazole group.

According to another exemplary embodiment, Ra is hydrogen; heavy hydrogen; A phenyl group unsubstituted or substituted with a halogen group or a butyl group; Naphthyl group; Or a dibenzofuran group.

In one embodiment of the present invention, R ₁ and R ₂ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); Silyl groups; Boron group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

According to another example, R ₁ and R ₂ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); Silyl groups; Boron group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In another example, R ₁ and R ₂ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); Silyl groups; Boron group; An alkyl group having 1 to 20 carbon atoms; A cycloalkyl group having 3 to 30 carbon atoms; Aryl groups having 6 to 30 carbon atoms; Or a heteroaryl group having 2 to 30 carbon atoms.

According to an example of the present invention, n1 is an integer of 0 to 2, and when n1 is 2, the substituents in parentheses are the same as or different from each other.

According to an example of the present invention, n1 is an integer of 0 to 2, and when n1 is 2, R1 is the same as or different from each other.

According to another example, n1 is 0 or 1.

According to an example of the present invention, n2 is an integer of 0 to 2, and when n2 is 2, R2 is the same as or different from each other.

According to another example, n2 is 0 or 1.

According to an embodiment of the present invention, B ₁ to B ₈ are the same as or different from each other, and each independently N, C (Rb) or C (Rb ').

In one embodiment of the present invention, at least one of B ₁ to B ₄ is C (Rb ' ), and at least one of the B ₅ to B ₈ is C (Rb').

In another exemplary embodiment, one of B ₁ to B ₄ is C (Rb '), and the other three are C (Rb).

According to another embodiment, one of the B ₁ to B ₄ is N, one is C (Rb '), the other two are C (Rb).

In another embodiment, two of the B ₁ to B ₄ is N, one is C (Rb '), the other is C (Rb).

In another exemplary embodiment, one of B ₅ to B ₈ is C (Rb '), and the other three are C (Rb).

According to another embodiment, one of the B ₅ to B ₈ is N, one is C (Rb '), the other two are C (Rb).

In another embodiment, two of the B ₅ to B ₈ is N, one is C (Rb '), the other is C (Rb).

According to an exemplary embodiment of the present invention, the Rb 'is a substituted or unsubstituted amine group; Or a heterocyclic group containing one or more substituted or unsubstituted N.

According to another exemplary embodiment, Rb 'is a substituted or unsubstituted arylamine group; Substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted cycloalkylarylamine group; Substituted or unsubstituted arylheteroarylamine group; Or a heterocyclic group containing one or more substituted or unsubstituted N. The aryl group may have 6 to 60 carbon atoms, the heteroaryl group and heterocyclic group may have 2 to 60 carbon atoms, and the cycloalkyl group may have 3 to 60 carbon atoms.

According to another exemplary embodiment, Rb 'is a substituted or unsubstituted arylamine group; Substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted cycloalkylarylamine group; Substituted or unsubstituted arylheteroarylamine group; Or a substituted or unsubstituted carbazole group. The aryl group may have 6 to 60 carbon atoms, the heteroaryl group and heterocyclic group may have 2 to 60 carbon atoms, and the cycloalkyl group may have 3 to 60 carbon atoms.

In another exemplary embodiment, Rb 'is 1 selected from the group consisting of deuterium, a halogen group, a silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. Substituted or unsubstituted arylamine group; A heteroarylamine group unsubstituted or substituted with one or more selected from the group consisting of deuterium, a halogen group, a silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A cycloalkylarylamine group unsubstituted or substituted with one or more selected from the group consisting of deuterium, a halogen group, a silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; An arylheteroarylamine group unsubstituted or substituted with one or more selected from the group consisting of deuterium, a halogen group, a silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or one or more substituted or unsubstituted N by one or more selected from the group consisting of deuterium, a halogen group, a silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. It is a heterocyclic group.

According to an exemplary embodiment of the present invention, at least one of B ₁ to B ₄ is C (Rb ′), Rb 'is a substituted or unsubstituted arylamine group; Substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted cycloalkylarylamine group; Substituted or unsubstituted arylheteroarylamine group; Or a heterocyclic group including one or more substituted or unsubstituted N, at least one of B ₅ to B ₈ is C (Rb '), and Rb' is a substituted or unsubstituted arylamine group; Substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted cycloalkylarylamine group; Substituted or unsubstituted arylheteroarylamine group; Or a heterocyclic group containing one or more substituted or unsubstituted N.

According to an exemplary embodiment of the present invention, the Rb is hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl groups; Boron group; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

According to another exemplary embodiment, Rb is hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl groups; Boron group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In another example, at least one of B ₁ to B ₄ is C (Rb '), Rb' is represented by the following Formula A, and at least one of B ₅ to B ₈ is C (Rb '). , Rb 'may be represented by the formula (A).

[Formula A]

In Chemical Formula A,

Ar ₁ and Ar ₂ are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted heteroaryl group, or combine with each other to form a substituted or unsubstituted hetero ring,

는 C에 결합되는 위치를 나타낸다.

Denotes the position at which C is bonded.

According to an example of the present invention, Ar ₁ and Ar ₂ are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, or combine with each other to form a substituted or unsubstituted hetero ring having 2 to 60 carbon atoms.

According to an example of the present invention, Ar ₁ and Ar ₂ are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, or combine with each other to form a substituted or unsubstituted hetero ring having 2 to 30 carbon atoms.

According to another example, Ar ₁ and Ar ₂ are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; A substituted or unsubstituted fluorenyl group; Substituted or unsubstituted benzofluorenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted cyclohexyl group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted carbazole group; Or a substituted or unsubstituted pyridine group, or combine with each other to form a substituted or unsubstituted carbazole group.

In another example, Ar ₁ and Ar ₂ are the same as or different from each other, and each independently deuterium, a halogen group, a silyl group, a substituted or unsubstituted C1-20 alkyl group, and a substituted or unsubstituted carbon number An aryl group having 6 to 60 carbon atoms substituted or unsubstituted with at least one selected from the group consisting of 6 to 30 aryl groups; Deuterium, halogen, silyl, substituted or unsubstituted C1-C20 alkyl group and substituted or unsubstituted C6-C30 aryl group having one or more substituted or unsubstituted C6-C60 cyclo An alkyl group; Or deuterium, halogen, silyl, substituted or unsubstituted C1-C20 alkyl group and substituted or unsubstituted C6-C30 aryl group having one or more substituted or unsubstituted carbon atoms of 2 to 60 Or a heteroaryl group, or bonded to each other, or substituted with one or more selected from the group consisting of deuterium, a halogen group, a silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. To form a ring heterocyclic ring having 2 to 60 carbon atoms.

According to another example, Ar ₁ and Ar ₂ are the same as or different from each other, and each independently deuterium, a halogen group, a silyl group, a substituted or unsubstituted C1-20 alkyl group and a substituted or unsubstituted carbon number A phenyl group unsubstituted or substituted with one or more selected from the group consisting of 6 to 30 aryl groups; A biphenyl group unsubstituted or substituted with one or more selected from the group consisting of deuterium, a halogen group, a silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A terphenyl group unsubstituted or substituted with one or more selected from the group consisting of deuterium, a halogen group, a silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Deuterium, halogen, silyl, substituted or unsubstituted C1-C20 alkyl group and substituted or unsubstituted C6-C30 aryl group selected from the group consisting of one or more substituted or unsubstituted fluorenyl group; A benzofluorenyl group unsubstituted or substituted with one or more selected from the group consisting of deuterium, a halogen group, a silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A naphthyl group unsubstituted or substituted with one or more selected from the group consisting of deuterium, a halogen group, a silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Phenanthrenyl groups unsubstituted or substituted with one or more selected from the group consisting of deuterium, a halogen group, a silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A cyclohexyl group unsubstituted or substituted with one or more selected from the group consisting of deuterium, a halogen group, a silyl group, a substituted or unsubstituted C1-C20 alkyl group and a substituted or unsubstituted C6-C30 aryl group; A dibenzofuran group unsubstituted or substituted with at least one selected from the group consisting of deuterium, a halogen group, a silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A debenzothiophene group unsubstituted or substituted with one or more selected from the group consisting of deuterium, a halogen group, a silyl group, a substituted or unsubstituted C1-C20 alkyl group and a substituted or unsubstituted C6-C30 aryl group; A desubstituted or unsubstituted carbazole group selected from the group consisting of deuterium, a halogen group, a silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Deuterium, a halogen group, a silyl group, a substituted or unsubstituted pyridine group having one or more selected from the group consisting of a substituted or unsubstituted C1-C20 alkyl group and a substituted or unsubstituted C6-C30 aryl group, or each other, or To form a substituted or unsubstituted carbazole group selected from the group consisting of deuterium, a halogen group, a silyl group, a substituted or unsubstituted C1-C20 alkyl group and a substituted or unsubstituted C6-C30 aryl group do.

In another embodiment, Ar ₁ and Ar ₂ are the same as or different from each other, and each independently a methyl group unsubstituted or substituted with deuterium, fluorine (-F), trimethylsilyl group, deuterium or fluorine (-F) A phenyl group unsubstituted or substituted with one or more selected from the group consisting of an ethyl group, a propyl group, a butyl group, a phenyl group, a biphenyl group and a naphthyl group; A biphenyl group unsubstituted or substituted with one or more selected from the group consisting of deuterium, fluorine (-F), trimethylsilyl group, methyl group, ethyl group, propyl group, butyl group, phenyl group, biphenyl group and naphthyl group; Terphenyl groups unsubstituted or substituted with one or more selected from the group consisting of deuterium, fluorine (-F), trimethylsilyl, methyl, ethyl, propyl, butyl, phenyl, biphenyl and naphthyl groups; Fluorenyl group unsubstituted or substituted with one or more selected from the group consisting of deuterium, fluorine (-F), trimethylsilyl, methyl, ethyl, propyl, butyl, phenyl, biphenyl and naphthyl groups; Benzofluorenyl group unsubstituted or substituted with one or more selected from the group consisting of deuterium, fluorine (-F), trimethylsilyl group, methyl group, ethyl group, propyl group, butyl group, phenyl group, biphenyl group and naphthyl group; A naphthyl group unsubstituted or substituted with one or more selected from the group consisting of deuterium, fluorine (-F), trimethylsilyl group, methyl group, ethyl group, propyl group, butyl group, phenyl group, biphenyl group and naphthyl group; Phenanthrenyl group unsubstituted or substituted with one or more selected from the group consisting of deuterium, fluorine (-F), trimethylsilyl, methyl, ethyl, propyl, butyl, phenyl, biphenyl and naphthyl groups; A cyclohexyl group unsubstituted or substituted with one or more selected from the group consisting of deuterium, fluorine (-F), trimethylsilyl group, methyl group, ethyl group, propyl group, butyl group, phenyl group, biphenyl group and naphthyl group; Dibenzofuran group unsubstituted or substituted with one or more selected from the group consisting of deuterium, fluorine (-F), trimethylsilyl, methyl, ethyl, propyl, butyl, phenyl, biphenyl and naphthyl groups; Dibenzothiophene group unsubstituted or substituted with deuterium, fluorine (-F), trimethylsilyl group, methyl group, ethyl group, propyl group, butyl group, phenyl group, biphenyl group and naphthyl group; Carba substituted or unsubstituted with one or more selected from the group consisting of deuterium, fluorine (-F), trimethylsilyl, methyl, ethyl, propyl, butyl, deuterium substituted or unsubstituted phenyl, biphenyl and naphthyl groups Dozing; A deuterium, fluorine (-F), trimethylsilyl group, methyl group, ethyl group, propyl group, butyl group, phenyl group, biphenyl group and one or more selected from the group consisting of a naphthyl group or a substituted or unsubstituted pyridine group, or combine with each other To form a substituted or unsubstituted carbazole group with a butyl group.

In one embodiment of the present specification, Chemical Formula 1 may be represented by any one of the following compounds.

"는 메틸기이며, 이중 결합을 중심으로 cis 형태 또는 trans 형태로 나타낼 수 있는 것을 의미한다.Bound to an alkenyl group in the compound "

"Is a methyl group, it means that can be represented in the cis form or trans form around the double bond.

In addition, in the compound, -Ph means a phenyl group.

Compound of Formula 1 according to an exemplary embodiment of the present specification may be prepared by the production method described below.

For example, the compound of Formula 1 may be prepared in the core structure as shown in the following scheme. Substituents may be combined by methods known in the art, and the type, position or number of substituents may be changed according to techniques known in the art.

<Scheme>

In the final product, X ₁ and X ₂ may be O or S, respectively, and when X ₁ and X ₂ are S (═O) or SO ₂ , respectively, they may be obtained by further oxidation.

Intermediate 3 (IM-3) is synthesized by a general Suzuki coupling reaction. Following ring closure reaction of intermediate 3, the hydroxyl group (hydroxyl group) can be made into a sulfone group (sulfone group) to make intermediate 4 (IM-4). It is possible to synthesize <Formula 1> by the Buckwaldamination between the intermediate 4 and various amine groups.

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

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

Moreover, the compound which has the intrinsic property of the introduced substituent can be synthesize | combined by introducing various substituents into the core structure of the above structure. For example, by incorporating a substituent mainly used in the hole injection layer material, the hole transport material, the light emitting layer material, and the electron transport layer material used in the manufacture of the organic light emitting device into the core structure, it is possible to synthesize a material satisfying the requirements of each organic material layer. Can be.

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

The organic light emitting device of the present invention may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except that at least one organic material layer is 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 in the manufacture of the organic light emitting device. Here, the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spraying method, roll coating and the like, but is not limited thereto.

The organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention includes a hole injection layer, a hole transport layer, a layer for simultaneously injecting and transporting holes as an organic material layer, a light emitting layer, an electron transport layer, an electron injection layer, a layer for simultaneously transporting electrons and electrons, and the like. It may have a structure. However, the structure of the organic light emitting device is not limited thereto and may include fewer organic layers or more organic 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 the electron injection layer may include the above-described compound.

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, the hole injection layer or a hole transport layer may include the above-described compound.

In another organic light emitting diode according to another exemplary embodiment, the organic material layer may include a light emitting layer, and the light emitting layer may include the compound described above.

According to another exemplary embodiment, the organic material layer may include a light emitting layer, and the light emitting layer may include the aforementioned compound as a dopant of the light emitting layer.

In another exemplary embodiment, the organic material layer may include a light emitting layer, and the light emitting layer may include the compound described above as a dopant of the light emitting layer and further include a host.

According to another exemplary embodiment, the organic material layer includes a light emitting layer, the light emitting layer may include the above-described compound as a dopant of the light emitting layer, and may further include the following Chemical Formula 1-A as a host.

[Formula 1-A]

In Chemical Formula 1-A,

Ar ₁ Ar ₃ is the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

L ₁ to L ₃ are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

R ₁₁ is hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); Nitro group; Silyl groups; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

q1 is an integer of 0-7, and when q1 is two or more, two or more R <_11> is same or different from each other.

According to an exemplary embodiment of the present invention, the Ar ₁ Ar ₃ is the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.

According to another exemplary embodiment, Ar ₁ Ar ₃ is the same as or different from each other, and each independently hydrogen; 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, Ar ₁ Ar ₃ is the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

According to another exemplary embodiment, Ar ₃ is hydrogen.

In another exemplary embodiment, Ar ₁ is hydrogen; Substituted or unsubstituted phenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted naphthobenzofuran group; Substituted or unsubstituted thiophene group; Or a substituted or unsubstituted indolocarbazole group.

According to another exemplary embodiment, Ar ₁ is hydrogen; Phenyl group unsubstituted or substituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms; A naphthyl group unsubstituted or substituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms; A dibenzofuran group unsubstituted or substituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms; Naphthobenzofuran group unsubstituted or substituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms; Thiophene groups unsubstituted or substituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms; Or an indolocarbazole group unsubstituted or substituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms.

In another exemplary embodiment, Ar ₁ is hydrogen; A phenyl group unsubstituted or substituted with deuterium; A naphthyl group unsubstituted or substituted with a methyl group; Dibenzofuran group; Naphthobenzofuran group; Thiophene group substituted with phenyl group; Or an indolocarbazole group.

According to an exemplary embodiment of the present invention, Ar ₂ is hydrogen; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to another exemplary embodiment, Ar ₂ is hydrogen; Substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group.

In another exemplary embodiment, Ar ₂ is hydrogen; Phenyl group unsubstituted or substituted with deuterium (D), a halogen group, a cyano group, a silyl group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms; A biphenyl group unsubstituted or substituted with deuterium (D), a halogen group, a cyano group, a silyl group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms; Or a naphthyl group unsubstituted or substituted with deuterium (D), a halogen group, a cyano group, a silyl group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms.

According to another exemplary embodiment, Ar ₂ is hydrogen; A phenyl group unsubstituted or substituted with a cyclohexyl group, a phenyl group or a naphthyl group; Biphenyl groups unsubstituted or substituted with deuterium, fluorine, cyano groups, or trimethylsilyl groups; Or a naphthyl group unsubstituted or substituted with a methyl group, a phenyl group, or a naphthyl group.

According to an exemplary embodiment of the present invention, L ₁ to L ₃ are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.

In another exemplary embodiment, L ₁ to L ₃ are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.

According to another exemplary embodiment, the L ₁ to L ₃ are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.

According to another exemplary embodiment, the L ₁ to L ₃ are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In another exemplary embodiment, L ₁ to L ₃ are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted phenylene group; Or a substituted or unsubstituted naphthylene group.

According to another exemplary embodiment, the L ₁ to L ₃ are the same as or different from each other, and each independently a direct bond; Phenylene group; Or a naphthylene group.

According to an exemplary embodiment of the present invention, R ₁₁ is hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); Nitro group; Silyl groups; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to another exemplary embodiment, R ₁₁ is hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); Nitro group; Silyl groups; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In another exemplary embodiment, R ₁₁ is hydrogen.

According to an exemplary embodiment of the present invention, q1 is an integer of 0 to 2.

In another exemplary embodiment, q1 is 0 or 1.

In one embodiment of the present specification, Chemical Formula 1-A may be represented by any one of the following compounds.

When the compound of the present invention is included as a dopant of the emission layer, and the chemical formula 1-A is included as a host, the content of the dopant may be 1 part by weight to 10 parts by weight based on 100 parts by weight of the host.

According to another exemplary embodiment, the organic material layer includes a light emitting layer, and the light emitting layer includes the above-mentioned compound as a dopant of the light emitting layer, and includes at least two of the compounds represented by the following Chemical Formulas 1-B and 1-C as hosts. It may further include.

 [Formula 1-B]

[Formula 1-C]

In Chemical Formulas 1-B and 1-C,

Ar ₄ to Ar ₈ are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted aryl group,

Ar ₉ is a substituted or unsubstituted heterocyclic group,

L ₄ to L ₉ are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

R ₁₂ and R ₁₃ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); Nitro group; Silyl groups; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

q2 and q3 are each an integer of 0 to 7, and when q2 and q3 are each 2 or more, the substituents in the parentheses are the same or different from each other.

According to an exemplary embodiment of the present invention, Ar ₄ to Ar ₈ are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

According to another exemplary embodiment, Ar ₄ to Ar ₈ are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to another exemplary embodiment, Ar ₆ and Ar ₈ are hydrogen.

In another exemplary embodiment, Ar ₅ and Ar ₇ are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group.

In another exemplary embodiment, Ar ₅ and Ar ₇ are the same as or different from each other, and each independently hydrogen; Phenyl group unsubstituted or substituted with deuterium (D), a halogen group, a cyano group, a silyl group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms; A biphenyl group unsubstituted or substituted with deuterium (D), a halogen group, a cyano group, a silyl group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms; Or a naphthyl group unsubstituted or substituted with deuterium (D), a halogen group, a cyano group, a silyl group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms.

According to another exemplary embodiment, Ar ₅ and Ar ₇ are the same as or different from each other, and each independently hydrogen; A phenyl group unsubstituted or substituted with a cyclohexyl group, a phenyl group or a naphthyl group; Biphenyl groups unsubstituted or substituted with deuterium, fluorine, cyano groups, or trimethylsilyl groups; Or a naphthyl group unsubstituted or substituted with a methyl group, a phenyl group, or a naphthyl group.

According to an exemplary embodiment of the present invention, Ar ₄ is hydrogen; Substituted or unsubstituted phenyl group; Or a substituted or unsubstituted naphthyl group.

According to another exemplary embodiment, Ar ₄ is hydrogen; Phenyl group unsubstituted or substituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms; Or a naphthyl group unsubstituted or substituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms.

In another exemplary embodiment, Ar ₄ is hydrogen; A phenyl group unsubstituted or substituted with deuterium; Or a naphthyl group unsubstituted or substituted with a methyl group.

According to an exemplary embodiment of the present specification, Ar ₉ is a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

According to another exemplary embodiment, Ar ₉ is a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In another exemplary embodiment, Ar ₉ is a substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted naphthobenzofuran group; Substituted or unsubstituted thiophene group; Or a substituted or unsubstituted indolocarbazole group.

According to another exemplary embodiment, Ar ₉ is a dibenzofuran group unsubstituted or substituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms; Naphthobenzofuran group substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms; Thiophene groups unsubstituted or substituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms; Or an indolocarbazole group unsubstituted or substituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms.

In another exemplary embodiment, Ar ₉ is a dibenzofuran group; Naphthobenzofuran group; Thiophene group substituted with phenyl group; Or an indolocarbazole group.

According to an exemplary embodiment of the present invention, L ₄ to L ₉ are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.

In another exemplary embodiment, L ₄ to L ₉ are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.

According to another exemplary embodiment, L ₄ to L ₉ are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.

According to another exemplary embodiment, L ₄ to L ₉ are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In another exemplary embodiment, L ₄ to L ₉ are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted phenylene group; Or a substituted or unsubstituted naphthylene group.

According to another exemplary embodiment, L ₄ to L ₉ are the same as or different from each other, and each independently a direct bond; Phenylene group; Or a naphthylene group.

According to an exemplary embodiment of the present invention, R ₁₂ and R ₁₃ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); Nitro group; Silyl groups; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to another exemplary embodiment, the R ₁₂ and R ₁₃ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group (-CN); Nitro group; Silyl groups; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In another exemplary embodiment, R ₁₁ and R ₁₂ are hydrogen.

According to an exemplary embodiment of the present specification, q2 is an integer of 0 to 7, and when q2 is 2 or more, two or more R ₁₂ are the same as or different from each other.

According to another exemplary embodiment, q2 is an integer of 0 to 2.

According to another exemplary embodiment, q2 is 0 or 1.

According to an exemplary embodiment of the present specification, q3 is an integer of 0 to 7, and when q3 is 2 or more, two or more R ₁₃ are the same as or different from each other.

According to another exemplary embodiment, q3 is an integer of 0 to 2.

According to another exemplary embodiment, q3 is 0 or 1.

In one embodiment of the present specification, Chemical Formula 1-B may be represented by any one of the following compounds.

In one embodiment of the present specification, Chemical Formula 1-C may be represented by any one of the following compounds.

When the compound of the present invention is included as a dopant of the light emitting layer, and includes two or more of the compounds represented by Formulas 1-B and 1-C as a host, the content of the dopant is 1 part by weight based on 100 parts by weight of the host. It may be 10 parts by weight.

According to another exemplary embodiment, the compound may be included as a dopant of the emission layer, and the compound represented by Formula 1-B and the compound represented by Formula 1-C may be included as a host of the emission layer. The mixed weight ratio of (1: B: 1-C) may be 95: 5 to 5:95.

In another exemplary embodiment, the organic material layer includes a light emitting layer, and the light emitting layer includes the aforementioned compound as a dopant of the light emitting layer, includes a fluorescent host or a phosphorescent host, and includes another organic compound, a metal, or a metal compound as a dopant. It may include.

As another example, the organic material layer may include a light emitting layer, and the light emitting layer may include the aforementioned compound as a dopant of the light emitting layer, include a fluorescent host or a phosphorescent host, and may be used with an iridium-based (Ir) dopant.

According to another exemplary embodiment, the organic material layer may include a light emitting layer, and the light emitting layer may include the aforementioned compound as a host of the light emitting layer.

As another example, the organic material layer may include a light emitting layer, the light emitting layer may be included as a host of the light emitting layer described above, and further include a dopant.

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 a 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 illustrates 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). In addition, the hole transport layer may be two or more layers.

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, and has a metal oxide or a metal oxide or an alloy thereof on a substrate. An organic material layer including a hole injection layer, a hole transport layer, a hole injection and hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a layer for simultaneously transporting electrons and electrons, etc. After forming, it can be prepared by depositing a material that can be used as a cathode thereon. In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

The organic material layer may be a multilayer structure including a hole injection layer, a hole transport layer, a layer for simultaneously injecting holes and transporting holes, a light emitting layer, an electron transport layer, an electron injection layer, a layer for simultaneously transporting and transporting electrons, and the like. It may be a single layer structure. In addition, the organic layer may be prepared by using a variety of polymer materials, and by using a method such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer, rather than a deposition method. It can be prepared in layers.

The anode is an electrode for injecting holes, and a material having a large work function is preferable as an anode material so that hole injection can be smoothly performed 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 and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of a metal and an 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, and the like, but are not limited thereto.

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

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

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

The emission layer may emit red, green, or blue light, and may be formed of a phosphor or a fluorescent material. The light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable. Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq ₃ ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.

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

Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, and include pyrene, anthracene, chrysene, and periplanthene having an arylamino group, and a styrylamine compound may be substituted or unsubstituted. At least one arylvinyl group is substituted with the substituted arylamine, and one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine and the like, but is not limited thereto. In addition, the metal complex includes, but is not limited to, an iridium complex, a platinum complex, and the like.

The electron transport layer may serve to facilitate the transport of electrons. As the electron transporting material, a material capable of injecting electrons well from the cathode and transferring the electrons to the light emitting layer is suitable. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes including Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The thickness of the electron transport layer may be 1 to 50 nm. If the thickness of the electron transporting layer is 1 nm or more, there is an advantage that the electron transporting property can be prevented from being lowered. If the thickness of the electron transporting layer is 50 nm or less, the thickness of the electron transporting layer is too thick to prevent the driving voltage from increasing to improve the movement of electrons. There is an advantage to this.

The electron injection layer may play a role of smoothly injecting electrons. As the electron injection material, it has the ability to transport electrons, has an electron injection effect from the cathode, excellent electron injection effect to the light emitting layer or the light emitting material, and prevents the movement of excitons generated in the light emitting layer to the hole injection layer, and The compound which is excellent in thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and derivatives thereof, metal Complex compounds, nitrogen-containing five-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) ( o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtolato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, It is not limited to this.

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

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

Hereinafter, the present invention will be described in detail with reference to Examples. However, the embodiments according to the present disclosure may be modified in various other forms, and the scope of the present application is not interpreted to be limited to the embodiments described below. Embodiments of the present application are provided to more fully describe the present specification to those skilled in the art.

< Synthesis Example >

Synthesis Example  One.

Starting material T-1 (50 g), starting material T-2 (20 g), bis (tri-tert-butylphosphine) palladium (0) under nitrogen atmosphere [Bis (tri-tert-butylphosphine) -palladium (0)] (0.25 g), aq. The flask containing K ₂ CO ₃ (82.2 g in 500 mL of water) and 1.5 L of tetrahydrofuran (THF) was heated and stirred for 2 hours. After cooling the reaction solution to room temperature, water and ethyl acetate were added and extracted and washed. The organic layer was recovered, the extraction solvent was removed, and the residue was purified by recrystallization (ethyl acetate / hexane) to obtain 30.3 g of intermediate A-1.

Mass [M + 1] = 431

Synthesis Example  2.

The flask containing Intermediate A-1 (27 g), K ₂ CO ₃ (44 g) and 1 L of N-methyl-2-pyrrilidone (NMP) was heated and stirred at 150 ° C. for 5 hours under a nitrogen atmosphere. After all of the intermediate A-1 was consumed, the reaction solution was cooled to 50 ° C., and then perfluorosulfonyl fluoride (114 g) was added dropwise using a dropping funnel. When intermediate A-2 became the main product, the reaction solution was cooled to room temperature and the resulting solid was filtered. The solid obtained by the filter was cooled by heating after stirring with heat using ethyl acetate / water, and the solid was filtered. The solid obtained by the filter was once again heated with stirring using THF / water and cooled to room temperature, and then the solid was filtered. The filtered solid was dried to obtain 31.1 g of intermediate A-2.

Synthesis Example  3.

Intermediate A-2 (10.0 g) and T-3 [bis (4- (tert-butyl) phenyl) amine, (6.2 g)], Bis (dibenzylidineacetone) palladium (0) (Pd (dba) ₂ , 0.18 g), Xphos (0.3 g), K ₃ PO ₄ (tripotassium phosphate, 7.8 g) and a flask containing 100 mL of toluene were refluxed and stirred for 24 hours. After cooling the reaction solution to room temperature, water and toluene were added and extracted and washed. The organic layer was recovered, the extraction solvent was removed, and the residue was purified by recrystallization (toluene / ethyl acetate) to obtain 3.2 g of Compound BD-A. 3 shows an MS measurement graph of BD-A.

Mass [M + 1] = 917

Synthesis Example  4.

2.6 g of Compound BD-B was obtained by the same method as the method of synthesizing Compound BD-A, except that T-4 was used instead of T-3 in Synthesis Example 3. 4 shows an MS measurement graph of BD-B.

Mass [M + 1] = 861

Synthesis Example  5.

2.6 g of Compound BD-C was obtained by the same method as the method of synthesizing Compound BD-A, except that T-5 was used instead of T-3 in Synthesis Example 3. 5 shows an MS measurement graph of BD-C.

Mass [M + 1] = 833

Synthesis Example  6.

29 g of Compound D-1 was obtained by the same method as the method of synthesizing Intermediate A-1, except that T-6 was used instead of T-2 in Synthesis Example 1.

Mass [M + 1] = 431

Synthesis Example  7.

28 g of Compound D-2 was obtained by the same method as the method of synthesizing Intermediate A-2, except that D-1 was used instead of A-1 in Synthesis Example 2.

Synthesis Example  8.

4.0 g of Compound BD-D was obtained by the same method as the method of synthesizing Compound BD-A, except that D-2 instead of A-2 and T-7 instead of T-3 were used in Synthesis Example 3. 6 shows a graph of MS measurement of BD-D.

Mass [M + 1] = 873

Synthesis Example  9.

2.9 g of Compound BD-E was obtained by the same method as the method for synthesizing Compound BD-A, except that D-2 instead of A-2 and T-8 instead of T-3 were used in Synthesis Example 3. 7 shows a graph of MS measurement of BD-E.

Mass [M + 1] = 749

Synthesis Example  10.

2.1 g of Compound BD-F was obtained by the same method as the method of synthesizing Compound BD-A, except that D-2 instead of A-2 and T-9 instead of T-3 were used in Synthesis Example 3.

Mass [M + 1] = 757

Synthesis Example  11.

Except for using T-10 instead of T-2 in Synthesis Example 1, 25.2g of intermediate G-1 was obtained by the same method as the method of synthesizing Intermediate A-1.

Mass [M + 1] = 431

Synthesis Example  12.

24.0 g of Compound G-2 was obtained by the same method as the method of synthesizing Intermediate A-2, except that G-1 was used instead of A-1 in Synthesis Example 2.

Synthesis Example  13.

In Synthesis Example 3, 1.7 g of Compound BD-G was obtained by the same method as the method for synthesizing Compound BD-A, except that G-2 instead of A-2 and T-11 instead of T-3 were used.

Mass [M + 1] = 749

Synthesis Example  14.

3.0 g of Compound BD-H was obtained by the same method as the method of synthesizing Compound BD-A, except that G-2 instead of A-2 and T-12 instead of T-3 were used in Synthesis Example 3.

Mass [M + 1] = 957

Synthesis Example  14.

In Synthesis Example 3, 1.9 g of Compound BD-I was obtained by the same method as the method of synthesizing Compound BD-A, except that G-2 instead of A-2 and T-13 instead of T-3 were used.

Mass [M + 1] = 689

< Example >

Example  One.

A glass substrate (corning 7059 glass) coated with ITO (Indium Tin Oxide) with a thickness of 1,000 Å was placed in distilled water in which a dispersant was dissolved, and ultrasonically washed. Fischer Co. products were used for the detergent, and Millipore Co. Secondly filtered distilled water was used as a filter of the product. After the ITO was washed for 30 minutes, the ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing the distilled water, the ultrasonic washing in the order of isopropyl alcohol, acetone, methanol solvent and dried.

The compound HAT was thermally vacuum deposited to a thickness of 50 kPa on the prepared ITO transparent electrode to form a hole injection layer. The following compound HT-A 1000 Pa was vacuum-deposited on the hole transport layer, and the compound HT-B 100 Pa was subsequently deposited. The light emitting layer was vacuum deposited to a thickness of 200 Å with BD-A at 2% by weight with BH-1 and dopant as a host.

Next, 300 μs of the compound ET-A and the compound Liq were deposited at a ratio of 1: 1, and 10 μg of magnesium (Mg) doped with 150 μm thick silver (Ag) and 1,000 μm thick aluminum were sequentially added thereto. By evaporation to form a cathode, 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 the aluminum was maintained at a deposition rate of 3 Å / sec to 7 Å / sec.

Example  2.

In Example 1, an organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound BD-C instead of the compound BD-A.

Example  3.

In Example 1, an organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound BD-D instead of the compound BD-A.

Example  4.

In Example 1, an organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound BD-F instead of the compound BD-A.

Example  5.

In Example 1, an organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound BD-I instead of the compound BD-A.

Example  6.

In Example 1, an organic light emitting diode was manufactured according to the same method as Example 1 except for using BH-2 instead of compound BH-1.

< Comparative example >

Comparative example  One.

In Example 1, an organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound BD-J instead of the compound BD-A.

Comparative example  2.

In Example 1, an organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound BD-K instead of the compound BD-A.

Comparative example  3.

In Example 1, an organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound BD-L instead of the compound BD-A.

The organic light emitting diodes of Examples 1 to 6 and Comparative Examples 1 to 3 measured driving voltage, luminous efficiency and color coordinate at a current density of 10 mA / cm ² , and 95% of the initial luminance at a current density of 20 mA / cm ² . The time to become (LT95) was measured. The results are shown in Table 1 below.

Example Host Dopant 10 mA / cm ² 20 mA / cm ² Driving voltage (v) Efficiency (cd / A) CIEy Life (hr), 95% Example 1 BH-1 BD-A 4.4 7.8 0.138 220 Example 2 BH-1 BD-C 4.5 7.2 0.121 222 Example 3 BH-1 BD-D 4.5 6.4 0.121 243 Example 4 BH-1 BD-F 4.4 7.2 0.135 176 Example 5 BH-1 BD-I 4.3 6.9 0.145 185 Example 6 BH-2 BD-A 4.3 6.2 0.139 227 Comparative Example 1 BH-1 BD-J 4.6 6.3 0.117 180 Comparative Example 2 BH-1 BD-K 4.4 5.4 0.164 149 Comparative Example 3 BH-1 BD-L 4.1 5.1 0.156 133

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 (13)

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

In Chemical Formula 1,
A is a substituted or unsubstituted benzene ring,
X ₁ and X ₂ are the same as or different from each other, and are each independently O, S, or N (Ra),
Ra, R ₁ and R ₂ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl groups; Boron group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
B ₁ to B ₈ are the same as or different from each other, and each independently N, C (Rb) or C (Rb '),
Rb is hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl groups; Boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
Rb 'is a substituted or unsubstituted amine group; Or a heterocyclic group containing one or more substituted or unsubstituted N,
At least one of B ₁ to B ₄ is C (Rb '), at least one of B ₅ to B ₈ is C (Rb'),
n1 is an integer of 0 to 2, when n1 is 2, R1 is the same as or different from each other,
n2 is an integer of 0 to 2, and when n2 is 2, R2 is the same as or different from each other. The method according to claim 1,
At least one of B ₁ to B ₄ is C (Rb ′), Rb 'is a substituted or unsubstituted arylamine group; Substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted cycloalkylarylamine group; Substituted or unsubstituted arylheteroarylamine group; Or a heterocyclic group containing one or more substituted or unsubstituted N,
At least one of B ₅ to B ₈ is C (Rb '), and Rb' is a substituted or unsubstituted arylamine group; Substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted cycloalkylarylamine group; Substituted or unsubstituted arylheteroarylamine group; Or a heterocyclic group containing one or more substituted or unsubstituted N. The method according to claim 1,
At least one of B ₁ to B ₄ is C (Rb '), and Rb' is represented by the following Formula A,
At least one of B ₅ to B ₈ is C (Rb '), and Rb' is a compound represented by Formula A:
[Formula A]

In Chemical Formula A,
Ar ₁ and Ar ₂ are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted heteroaryl group, or combine with each other to form a substituted or unsubstituted hetero ring,

Denotes the position at which C is bonded. The method according to claim 1,
Formula 1 is a compound represented by any one of the following formulas 2 to 4:
[Formula 2]

[Formula 3]

[Formula 4]

In Chemical Formulas 2 to 4,
X ₁ and X ₂ are the same as or different from each other, and are each independently O, S, or N (Ra),
Z ₁ to Z ₆ , Ra, R ₁ and R ₂ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl groups; Boron group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
B ₁ to B ₈ are the same as or different from each other, and each independently N, C (Rb) or C (Rb '),
Rb is hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl groups; Boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
Rb 'is a substituted or unsubstituted amine group; Or a heterocyclic group containing one or more substituted or unsubstituted N,
At least one of B ₁ to B ₄ is C (Rb '), at least one of B ₅ to B ₈ is C (Rb'),
n1 is an integer of 0 to 2, when n1 is 2, R1 is the same as or different from each other,
n2 is an integer of 0 to 2, and when n2 is 2, R2 is the same as or different from each other. The method according to claim 1,
Formula 1 is a compound represented by any one of the following formula 1-1 to 1-6:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

In Chemical Formulas 1-1 to 1-6,
X ₁ and X ₂ are the same as or different from each other, and are each independently O, S, or N (Ra),
Z ₂₁ to Z ₃₂ , Ra, R ₁ and R ₂ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl groups; Boron group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
B ₁ to B ₈ are the same as or different from each other, and each independently N, C (Rb) or C (Rb '),
Rb is hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl groups; Boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
Rb 'is a substituted or unsubstituted amine group; Or a heterocyclic group containing one or more substituted or unsubstituted N,
At least one of B ₁ to B ₄ is C (Rb '), at least one of B ₅ to B ₈ is C (Rb'),
n1 is an integer of 0 to 2, when n1 is 2, R1 is the same as or different from each other,
n2 is an integer of 0 to 2, and when n2 is 2, R2 is the same as or different from each other. The method according to claim 1,
Formula 1 is the following compounds Compound represented by any of:

. A first electrode; A second electrode provided to face the first electrode; And an organic light emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound according to any one of claims 1 to 6. . The method according to claim 7,
The organic material layer includes a hole injection layer or a hole transport layer, the hole injection layer or hole transport layer comprises an organic light emitting device comprising the compound. The method according to claim 7,
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 the compound. The method according to claim 7,
The organic material layer includes an emission layer, and the emission layer includes the compound. The method according to claim 7,
The organic material layer includes an emission layer, and the emission layer includes the compound as a dopant of the emission layer. The method according to claim 11,
The light emitting layer is an organic light emitting device further comprising Formula 1-A as a host:
[Formula 1-A]

In Chemical Formula 1-A,
Ar ₁ Ar ₃ is the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
L ₁ to L ₃ are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
R ₁₁ is hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Silyl groups; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
q1 is an integer of 0-7, and when q1 is two or more, two or more R <_11> is same or different from each other. The method according to claim 11,
The organic light emitting device further comprises at least two of the compounds represented by the following formula 1-B and formula 1-C as a host:
[Formula 1-B]

[Formula 1-C]

In Chemical Formulas 1-B and 1-C,
Ar ₄ to Ar ₈ are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted aryl group,
Ar ₉ is a substituted or unsubstituted heterocyclic group,
L ₄ to L ₉ are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
R ₁₂ and R ₁₃ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Silyl groups; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
q2 and q3 are each an integer of 0 to 7, and when q2 and q3 are each 2 or more, the substituents in the parentheses are the same or different from each other.

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