KR20190116946A - Multicyclic compound and organic electronic device comprising the same - Google Patents

Abstract

The present specification provides a compound of chemical formula 1 and an organic electronic 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 electronic device. When manufacturing the organic electronic device including the compound according to at least one embodiment, it is possible to obtain the organic electronic device having high efficiency and long lifespan.

Description

Polycyclic compound and organic electronic device including the same {MULTICYCLIC COMPOUND AND ORGANIC ELECTRONIC DEVICE COMPRISING THE SAME}

This specification claims the benefit of Korean Patent Application No. 10-2018-0039760, filed April 5, 2018 with the Korean Intellectual Property Office, the entire contents of which are incorporated herein.

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

Representative examples of the organic electronic device is an organic light emitting device. In general, the organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy using organic materials. 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. In this case, 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.

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

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

Japanese public publication no. 2014-154615

In the present specification, a compound and an organic electronic 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,

R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Silyl groups; Boron group; Hydroxyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted alkylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylalkylamine group; Substituted or unsubstituted arylheteroarylamine group; Substituted or unsubstituted alkylheteroarylamine group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

Ar1 to Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Silyl groups; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

n1 is an integer of 0 to 3, when n1 is 2 or more, two or more R1 are the same as or different from each other,

n2 is an integer of 0 to 5, and when n2 is 2 or more, two or more R2 are the same or different from each other.

In addition, the present invention is 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 aforementioned compound.

The compound described herein can be used as the material of the organic material layer of the organic electronic device. When manufacturing an organic electronic device including a compound according to at least one embodiment, it is possible to obtain an organic electronic device having high efficiency and long life.

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 shows a MS measurement graph of compound BD-2.
4 shows a MS measurement graph of compound BD-3.
5 shows a MS measurement graph of compound BD-6.

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 Chemical Formula 1 is used in the organic material layer of the organic electronic device, since the structure of the luminophore is simple and rigid, the full width at half maximum is relatively improved, thereby achieving high efficiency. In addition, since dibenzofuran is more chemically stable, when manufacturing an organic electronic device comprising the compound represented by the formula (1) of the present invention, the life characteristics of the organic electronic device are always.

[Formula 1]

In Chemical Formula 1,

R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Silyl groups; Boron group; Hydroxyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted alkylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylalkylamine group; Substituted or unsubstituted arylheteroarylamine group; Substituted or unsubstituted alkylheteroarylamine group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

Ar1 to Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Silyl groups; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

n1 is an integer of 0 to 3, when n1 is 2 or more, two or more R1 are the same as or different from each other,

n2 is an integer of 0 to 5, and when n2 is 2 or more, two or more R2 are the same 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; Halogen group; Cyano group (-CN); Nitro group; Silyl groups; Boron group; Hydroxyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted alkylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylalkylamine group; Substituted or unsubstituted arylheteroarylamine group; Substituted or unsubstituted alkylheteroarylamine group; A substituted or unsubstituted cycloalkyl 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, but are not limited thereto. 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, hexyl group, n -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 alkoxy group may be linear, branched or cyclic. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C20. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, and the like, but is not limited thereto. .

Substituents comprising alkyl groups, alkoxy groups and other alkyl group moieties described herein include both straight and pulverized forms.

In the present specification, the aryl group in the aryloxy group may be described with reference to the aryl group described below.

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, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, and the like, but are not limited thereto.

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 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 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 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, for example, a phenyl group, a biphenyl group, a terphenyl group, a quarterphenyl group, etc., but is not limited thereto. The polycyclic aryl group may be naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, peryllenyl group, triphenyl group, chrysenyl group, fluorenyl group, benzofluorenyl group, triphenylenyl group, etc. It is not limited to this.

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, dibenzofuranyl group, dibenzothiophenyl group, carbazole group, Benzocarbazole groups, naphthobenzofuranyl groups, benzonaphthothiophenyl groups and the like, but are not limited thereto.

)을 들 수 있다.In the present specification, the hydrocarbon ring group may be an aromatic, aliphatic or a condensed ring of aromatic and aliphatic, and the description of the aforementioned aryl group may be applied except that the aromatic hydrocarbon ring is not monovalent, and the aliphatic hydrocarbon ring The description of the cycloalkyl group described above may be applied except that is not a monovalent group. In addition, an example of the condensed ring of the aromatic and aliphatic is hydronaphthalene, specifically 1,2,3,4-tetrahydronaphthalene (

).

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

According to an embodiment of the present invention, the compound of the present invention may have a maximum emission peak of 430 nm to 470 nm, and when the compound includes the compound in the light emitting layer of the organic electronic device, it emits blue light.

According to an exemplary embodiment of the present invention, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Silyl groups; Boron group; Hydroxyl group; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; Substituted or unsubstituted aryloxy group having 6 to 60 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 40 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 heterocyclic group having 2 to 60 carbon atoms.

According to another exemplary embodiment, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Silyl groups; Boron group; Hydroxyl group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; Substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms; A substituted or unsubstituted alkenyl group having 2 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 heterocyclic group having 2 to 30 carbon atoms.

In another exemplary embodiment, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; 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; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to another exemplary embodiment, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Silyl groups; An alkyl group having 1 to 20 carbon atoms; A cycloalkyl group having 3 to 30 carbon atoms; Or an aryl group having 6 to 30 carbon atoms.

In another exemplary embodiment, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Trimethylsilyl group; Substituted or unsubstituted methyl group; A substituted or unsubstituted cyclohexyl group; Or a substituted or unsubstituted phenyl group.

According to another exemplary embodiment, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Trimethylsilyl group; Methyl group; Cyclohexyl group; Or a phenyl group.

According to an exemplary embodiment of the present invention, n1 is an integer of 0 to 2.

According to another exemplary embodiment, n1 is 0 or 1.

According to an exemplary embodiment of the present invention, n2 is an integer of 0 to 2.

According to another exemplary embodiment, n2 is 0 or 1.

According to an exemplary embodiment of the present invention, Ar1 to Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Silyl groups; Boron group; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted hydrocarbon ring having 3 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

In another exemplary embodiment, Ar1 to Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Silyl groups; Boron group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted hydrocarbon ring having 3 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

According to another exemplary embodiment, Ar1 to Ar4 are the same as or different from each other, and each independently substituted or unsubstituted 3 to 60 hydrocarbon ring groups; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

In another exemplary embodiment, Ar1 to Ar4 are the same as or different from each other, and each independently substituted or unsubstituted hydrocarbon ring having 3 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

According to another exemplary embodiment, Ar1 to Ar4 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; A substituted or unsubstituted fluorenyl group; Substituted or unsubstituted benzofluorenyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted hydronaphthalene; Substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted carbazole group.

In another exemplary embodiment, Ar1 to Ar4 are the same as or different from each other, and each independently deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substitution Or a phenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of an unsubstituted heterocyclic group or a substituent to which two or more substituents are linked; A deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group substituted with one or more substituents or substituents connected with two or more substituents Or an unsubstituted biphenyl group; A deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group substituted with one or more substituents or substituents connected with two or more substituents Or an unsubstituted terphenyl group; A deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group substituted with one or more substituents or substituents connected with two or more substituents Or an unsubstituted naphthyl group; A deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group substituted with one or more substituents or substituents connected with two or more substituents Or an unsubstituted fluorenyl group; A deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group substituted with one or more substituents or substituents connected with two or more substituents Or an unsubstituted benzofluorenyl group; A deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group substituted with one or more substituents or substituents connected with two or more substituents Or an unsubstituted phenanthrenyl group; A deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group substituted with one or more substituents or substituents connected with two or more substituents Or unsubstituted hydronaphthalene; A deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group substituted with one or more substituents or substituents connected with two or more substituents Or an unsubstituted dibenzofuran group; Or a substituent having one or more substituents or two or more substituents selected from the group consisting of deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group. Substituted or unsubstituted carbazole group.

In another exemplary embodiment, Ar1 to Ar4 are the same as or different from each other, and each independently deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted A phenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of an aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or a substituent to which two or more substituents are linked; Deuterium, halogen, silyl, cyano, substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms A biphenyl group unsubstituted or substituted with one or more substituents selected from the group or a substituent to which two or more substituents are linked; Deuterium, halogen, silyl, cyano, substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms Terphenyl groups unsubstituted or substituted with at least one substituent selected from the group or at least two substituents linked thereto; Deuterium, halogen, silyl, cyano, substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms A naphthyl group unsubstituted or substituted with at least one substituent selected from the group or at least two substituents linked thereto; Deuterium, halogen, silyl, cyano, substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms A fluorenyl group unsubstituted or substituted with at least one substituent selected from the group or at least two substituents connected thereto; Deuterium, halogen, silyl, cyano, substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms A benzofluorenyl group unsubstituted or substituted with at least one substituent selected from the group or at least two substituents linked thereto; Deuterium, halogen, silyl, cyano, substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms A phenanthrenyl group unsubstituted or substituted with at least one substituent selected from the group or at least two substituents linked thereto; Deuterium, halogen, silyl, cyano, substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms Hydronaphthalene unsubstituted or substituted with at least one substituent selected from the group or at least two substituents linked thereto; Deuterium, halogen, silyl, cyano, substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms A dibenzofuran group unsubstituted or substituted with at least one substituent selected from the group or at least two substituents connected thereto; Or deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms. It is a carbazole group unsubstituted or substituted with one or more substituents or two or more substituents selected from the group consisting of.

In another exemplary embodiment, Ar1 to Ar4 are the same as or different from each other, and each independently deuterium, a halogen group, a cyano group, a trimethylsilyl group, a trifluoromethyl group, a methyl group, an ethyl group, a tert-butyl group, or a phenyl group a phenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of a tert-butylphenyl group and a carbazole group or a substituent to which two or more substituents are linked; A substituent to which one or more substituents or two or more substituents selected from the group consisting of deuterium, halogen, cyano, trimethylsilyl, trifluoromethyl, methyl, ethyl, tert-butyl, phenyl, tert-butylphenyl and carbazole groups A biphenyl group unsubstituted or substituted with; A substituent to which one or more substituents or two or more substituents selected from the group consisting of deuterium, halogen, cyano, trimethylsilyl, trifluoromethyl, methyl, ethyl, tert-butyl, phenyl, tert-butylphenyl and carbazole groups Terphenyl group unsubstituted or substituted with; A substituent to which one or more substituents or two or more substituents selected from the group consisting of deuterium, halogen, cyano, trimethylsilyl, trifluoromethyl, methyl, ethyl, tert-butyl, phenyl, tert-butylphenyl and carbazole groups Substituted or unsubstituted naphthyl group; A substituent to which one or more substituents or two or more substituents selected from the group consisting of deuterium, halogen, cyano, trimethylsilyl, trifluoromethyl, methyl, ethyl, tert-butyl, phenyl, tert-butylphenyl and carbazole groups A fluorenyl group unsubstituted or substituted with; A substituent to which one or more substituents or two or more substituents selected from the group consisting of deuterium, halogen, cyano, trimethylsilyl, trifluoromethyl, methyl, ethyl, tert-butyl, phenyl, tert-butylphenyl and carbazole groups Substituted or unsubstituted benzofluorenyl group; A substituent to which one or more substituents or two or more substituents selected from the group consisting of deuterium, halogen, cyano, trimethylsilyl, trifluoromethyl, methyl, ethyl, tert-butyl, phenyl, tert-butylphenyl and carbazole groups Substituted or unsubstituted phenanthrenyl group; A substituent to which one or more substituents or two or more substituents selected from the group consisting of deuterium, halogen, cyano, trimethylsilyl, trifluoromethyl, methyl, ethyl, tert-butyl, phenyl, tert-butylphenyl and carbazole groups Hydronaphthalene unsubstituted or substituted with; A substituent to which one or more substituents or two or more substituents selected from the group consisting of deuterium, halogen, cyano, trimethylsilyl, trifluoromethyl, methyl, ethyl, tert-butyl, phenyl, tert-butylphenyl and carbazole groups Substituted or unsubstituted dibenzofuran group; Or one or more substituents or two or more substituents selected from the group consisting of deuterium, halogen, cyano, trimethylsilyl, trifluoromethyl, methyl, ethyl, tert-butyl, phenyl, tert-butylphenyl and carbazole groups Or a carbazole group unsubstituted or substituted with a substituent.

According to an exemplary embodiment of the present invention, Formula 1 may be represented by any one of the following compounds.

The compound of Formula 1 may be prepared in the core structure through the same process as 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>

The above reaction scheme is only an example of a method of preparing a core structure of a compound according to an exemplary embodiment of the present invention and linking substituents, but is not limited thereto.

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 introducing a substituent mainly used in the hole injection layer material, the hole transport material, electron suppression material, the light emitting layer material and the electron transport layer material used in the manufacture of the organic light emitting device to meet the requirements of each organic layer. The substance to make can be synthesize | combined.

In addition, the organic electronic 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 electronic device of the present invention may be manufactured by a conventional method and material for manufacturing an organic electronic device, except that at least one organic material layer is formed using the above-described compound.

According to an exemplary embodiment of the present invention, the organic electronic device may be selected from the group consisting of an organic light emitting device, an organic phosphorescent device, an organic solar cell, an organic photoconductor (OPC) and a glass transistor.

Hereinafter, an organic light emitting diode will be exemplified.

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 is a hole injection layer, a hole transport layer, a hole injection layer and a hole transport layer at the same time, an electron suppression layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron injection and an electron transport layer simultaneously It may have a structure including the. However, the structure of the organic light emitting device is not limited thereto, and may include fewer 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, the electron transport layer or an 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 this case, the hole injection layer or the hole transport layer may be made of only the above-described compounds, but the compound may be present in a mixed or doped state with other hole injection layers or hole transport layer materials known in the art.

In the organic light emitting device of the present invention, the organic material layer includes a light emitting layer, and the light emitting layer includes 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,

A1 to A3 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

L1 to L3 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,

R11 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 R11 is same or different from each other.

According to an exemplary embodiment of the present invention, A1 to A3 are 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, A1 to A3 are 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, A1 to A3 are 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, A3 is hydrogen.

In another exemplary embodiment, A1 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 yet another exemplary embodiment, A1 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, A1 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, A2 is hydrogen; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to another exemplary embodiment, A2 is hydrogen; Substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group.

In another exemplary embodiment, A2 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, A2 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, L1 to L3 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, L1 to L3 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 L1 to L3 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 L1 to L3 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, L1 to L3 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 L1 to L3 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, R11 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, R11 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, R11 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,

A4 to A8 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted aryl group,

A9 is a substituted or unsubstituted heterocyclic group,

L4 to L9 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,

R12 and R13 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, A4 to A8 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, A4 to A8 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, A6 and A8 are hydrogen.

In another exemplary embodiment, A5 and A7 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, A5 and A7 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, A5 and A7 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, A4 is hydrogen; Substituted or unsubstituted phenyl group; Or a substituted or unsubstituted naphthyl group.

According to another exemplary embodiment, A4 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, A4 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, A9 is a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

According to another exemplary embodiment, A9 is a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In another exemplary embodiment, A9 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, A9 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, A9 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, L4 to L9 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, L4 to L9 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 L4 to L9 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 L4 to L9 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, L4 to L9 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 L4 to L9 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, R12 and R13 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, R12 and R13 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, R12 and R13 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 R12 are the same 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 R13 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 emission 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, and the light emitting layer may include the aforementioned compound as a host of the light emitting layer and further include a dopant.

In the organic light emitting device of the present invention, the organic material layer may include an electron suppression layer, and the electron suppression layer may include the aforementioned compound.

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.

For example, the organic light emitting diode may have a laminated structure as described below, but is not limited thereto.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

The structure of the organic light emitting device of the present 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).

For example, the organic light emitting device according to the present invention is a metal oxide or a metal oxide or alloy thereof having a conductivity on a substrate by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation To form an anode, and a hole injection layer, a hole transport layer, a hole injection and hole transport at the same time, a light emitting layer, an electron suppression layer, an electron transport layer, an electron injection layer and a layer for simultaneously injecting and transporting electrons After forming an organic material layer comprising a, 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 and transporting electrons, an electron suppression layer, a light emitting layer and an electron transport layer, an electron injection layer, a layer for simultaneously injecting and transporting electrons, and the like. However, the present invention is not limited thereto and may have a single layer structure. In addition, the organic material layer using a variety of polymer materials less or more by a solvent process (e.g. spin coating, dip coating, doctor blading, screen printing, inkjet printing or thermal transfer method) rather than deposition It can be prepared in a number of 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, 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 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 hole transport layer may be formed in one or more layers in the organic light emitting device. have.

A hole buffer layer may be additionally provided between the hole injection layer and the hole transport layer, and may include a hole injection or transport material known in the art.

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

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.

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

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

The electron transport layer may serve to facilitate the transport of electrons. As the electron 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 of transporting electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, prevents 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 derivatives thereof, metal Complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, 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 A-1 (80 g), starting material A-2 (87.5 g), bis (tri-tert-butylphosphine) palladium (0) under nitrogen atmosphere [Bis (tri-tert-butylphosphine) -palladium (0) (0.38 g), aq. The flask containing K ₂ CO ₃ (152.6 g in 300 mL of water) and 900 mL tetrahydrofuran (THF) was stirred at 50 ° C. for 5 hours. After cooling the reaction solution to room temperature, water and ethyl acetate were added and extracted and washed. The organic layer was recovered to remove the extraction solvent, to obtain intermediate A-3.

A flask containing A-3, K ₂ CO ₃ (44 g) and 1 L of N-methyl-2-pyrrilidone (NMP), which was not further purified under a nitrogen atmosphere, was heated and stirred at 150 ° C. for 5 hours. After the reaction was completed, the reaction solution was cooled to room temperature, 700 mL of water was added, and further stirred for 30 minutes. The solid obtained by filtration of the produced solid was ethyl acetate and sat. aq. After separation using NH ₄ Cl, the organic layer was recovered, filtered and treated with MgSO ₄ (anhydrous). The solvent of the filtered solution was distilled off under reduced pressure, recrystallized (Hexane) and dried to obtain 58.4 g of intermediate A-4.

Synthesis Example  2.

30 g of Intermediate A-4 was dissolved in 300 mL of acetonitrile, an aqueous potassium carbonate solution (46 g in H ₂ O 100 mL) was added at room temperature, and 67.5 g of nonafluorbutanesulfonyl fluoride was added dropwise. . After stirring for 2 hours, 200mL of water was added to the reaction and stirred for 30 minutes. The solid obtained by filtration of the produced solid was ethyl acetate and sat. aq. After separation using NH ₄ Cl, the organic layer was recovered, filtered and treated with Na ₂ SO ₄ (anhydrous). The solvent of the filtered solution was distilled off under reduced pressure, recrystallized (Ethyl acetate / Hexane) and dried to obtain 41 g of intermediate A-5.

Synthesis Example  3.

4 g of intermediate A-5 under nitrogen atmosphere, 4.8 g of bis (4- (tert-butyl) phenyl) amine, 7 g of potassium phosphate, bis (di Benzylideneacetone) palladium (0) [Bis (dibenzylideneacetone) palladium (0)] 0.12 g of Pd (dba) ₂ and 0.19 g of Xphos were put in 100 mL of dioxane, heated at 100 ° C. and stirred for 36 hours. After the completion of the reaction, the reaction mixture was cooled to room temperature, separated by addition of water and aq.NH ₄ Cl, and then filtered through MgSO ₄ (anhydrous), and the filtrate was distilled off under reduced pressure, followed by column chromatography (EA / Hx =). Purified by the method 30/1), 3.1 g of Compound BD-1 was obtained.

As a result of mass spectrum measurement of the obtained solid, a peak was confirmed at [M + H +] = 777.

Synthesis Example  4.

In the same manner as the synthesis of Compound BD-1 of Synthesis Example 3, 3.0 g of Compound BD-2 was synthesized.

The MS measurement graph of the compound BD-2 is shown in FIG. 3, and a peak was confirmed at [M + H +] = 897.

Synthesis Example  5.

In the same manner as the synthesis of Compound BD-1 of Synthesis Example 3, 4.0 g of Compound BD-3 was synthesized.

The MS measurement graph of the compound BD-3 is shown in FIG. 4, and a peak was confirmed at [M + H +] = 937.

Synthesis Example  6.

In the same manner as the synthesis of Compound BD-1 of Synthesis Example 3, 2.9 g of Compound BD-4 was synthesized.

As a result of mass spectrum measurement of the obtained solid, a peak was confirmed at [M + H +] = 913.

Synthesis Example  7.

In the same manner as the synthesis of Compound BD-1 of Synthesis Example 3, 2.7 g of Compound BD-5 was synthesized.

As a result of mass spectrum measurement of the obtained solid, a peak was confirmed at [M + H +] = 913.

Synthesis Example  8.

In the same manner as the synthesis of Compound BD-1 of Synthesis Example 3, 3.8 g of Compound BD-6 was synthesized.

The MS measurement graph of the compound BD-6 is shown in FIG. 5, and a peak was confirmed at [M + H +] = 997.

Synthesis Example  9.

In the same manner as the synthesis of Compound BD-1 of Synthesis Example 3, 2.9 g of Compound BD-7 was synthesized.

The mass spectrum measurement of the obtained solid showed a peak at [M + H +] = 997.

Synthesis Example  10.

In the same manner as the synthesis of Compound BD-1 of Synthesis Example 3, 2.2 g of Compound BD-8 was synthesized.

As a result of mass spectrum measurement of the obtained solid, a peak was confirmed at [M + H +] = 905.

Synthesis Example  11.

In the same manner as the synthesis of Compound BD-1 of Synthesis Example 3, 2.7 g of Compound BD-9 was synthesized.

Mass spectrum measurement of the obtained solid showed a peak at [M + H +] = 767.

Synthesis Example  12.

4.2 g of compound BD-10 was synthesized in the same manner as the method for synthesizing compound BD-1 of Synthesis Example 3.

Mass spectrum measurement of the obtained solid showed a peak at [M + H +] = 1141.

Synthesis Example  13.

Under a nitrogen atmosphere, a flask containing 28 g of intermediate A-4, 5 g of NaH, and 400 mL of dimethylformamide (DMF) was stirred at 0 ° C. for 30 minutes. Then, 21 g of 4-methoxybenzyl chloride was added, followed by stirring at room temperature for 8 hours. After the reaction was completed 400ml of water and stirred for 30 minutes. The solid obtained by filtration of the produced solid was ethyl acetate and sat. aq. After separation using NH ₄ Cl, the organic layer was collected, filtered and treated with Mg ₂ SO ₄ (anhydrous). The solvent of the filtered solution was distilled off under reduced pressure, recrystallized (Ethyl acetate / Hexane) and dried to obtain 31 g of an intermediate B-1.

41.5 mL of n-Butyllithium (2.5 M in hexane) was slowly added dropwise to a flask containing 31 g of intermediate B-1 dissolved in 300 mL of tetrahydrofuran (anhydrous) cooled to 0 ° C. under a nitrogen atmosphere. Stirred for 1 hour. Bromine 13g was slowly added dropwise at 0 ° C, and then the temperature was raised to room temperature and stirred for 3 hours. After completion of the reaction sat. NaS ₂ O ₃ and aq. NaCl was added thereto for separation, and then filtered through MgSO ₄ (anhydrous) treatment. The filtered solution was distilled off under reduced pressure and purified by recrystallization (ethylacetate / hexane) to give 23g of intermediate B-2.

Synthesis Example  14.

In the same manner as the synthesis of Intermediate A-3 of Synthesis Example 1, Intermediate B-3 was synthesized and the next reaction was carried out without further purification.

The flask containing intermediate B-3, 9.5 g of DDQ (2,3-dichloro-5,6-dicyano-p-benzoquinone), 130 mL of CHCl ₃ and 20 mL of water is stirred at room temperature for 2 hours. After the reaction was completed, the reaction solution was filtered through celite, and the filtrate was purified by aq. NaCl was added thereto for separation, and then filtered through MgSO ₄ (anhydrous) treatment. The filtered solution was distilled off under reduced pressure to obtain intermediate B-4 without further purification.

Intermediate B-5 was synthesized in the same manner as the synthesis of Intermediate A-5 of Synthesis Example 2, and 11 g of Intermediate B-5 was obtained by column chromatography (eluent: ethylacetate / hexane).

Synthesis Example  15.

In the same manner as the synthesis of Compound BD-1 of Synthesis Example 3, 2.5 g of Compound BD-11 was synthesized using Intermediate B-5.

As a result of mass spectrum measurement of the obtained solid, a peak was confirmed at [M + H +] = 917.

Synthesis Example  16.

In the same manner as the synthesis of Compound BD-1 of Synthesis Example 3, 2.2 g of Compound BD-12 was synthesized using Intermediate B-5.

As a result of mass spectrum measurement of the obtained solid, a peak was confirmed at [M + H +] = 865.

Synthesis Example  17.

In a flask containing 10 g of intermediate B-2 dissolved in 80 mL of tetrahydrofuran (anhydrous) cooled to -78 ° C under nitrogen atmosphere, 8.6 mL of n-Butyllithium (2.5 M in hexane) was slowly added dropwise. After that, the mixture was stirred for 30 minutes. 3.5 mL of chlorotrimethylsilane was slowly added dropwise at -78 ° C, then stirred for an additional 30 minutes at the same temperature, and then slowly raised to room temperature and stirred for 6 hours. After completion of the reaction, sat. NH ₄ Cl was added thereto for separation, followed by Na ₂ SO ₄ (anhydrous) treatment. Intermediate C-1 was obtained without further purification and the next reaction proceeded.

In the same manner as the method for synthesizing Intermediate B-5 from Intermediate B-3 of Synthesis Example 14, 7.4 g of Intermediate C-3 was obtained using Intermediate C-1.

Synthesis Example  18.

In the same manner as in the synthesis of Compound BD-1 of Synthesis Example 3, Compound BD-13 was synthesized using Intermediate C-3 and 1.76 g of Compound BD-13 (eluent: toluene / hexane) was synthesized. It was.

The mass spectrum measurement of the obtained solid showed a peak at [M + H +] = 837.

< 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 at 2 wt% with BH-1 and dopant as a host.

Thereafter, 300 Å of Compound ET-A and Liq were deposited at a 1: 1 ratio, and sequentially deposited 150 Å thick silver (Ag), 10 wt% doped magnesium (Mg), and 1,000 Å thick aluminum were deposited. The cathode was formed to manufacture an organic light emitting device.

In the above process, the deposition rate of the organic material was maintained at 1 Å / sec, LiF was 0.2 Å / sec, and 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-3 instead of the compound BD-2.

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-6 instead of the compound BD-2.

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-8 instead of the compound BD-2.

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-11 instead of the compound BD-2.

Example  6.

In Example 1, an organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound BD-13 instead of the compound BD-2.

Example  7.

In Example 1, an organic light emitting diode was manufactured according to the same method as Example 1 except for further including Compound BH-2 (weight ratio of BH-1 and BH-2: 1: 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 D-1 instead of the compound BD-2.

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 D-2 instead of the compound BD-2.

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 D-3 instead of the compound BD-2.

Comparative 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 D-4 instead of the compound BD-2.

The Examples 1 to 7 and Comparative Examples 1 to the driving voltage of the organic light-emitting element 4 at a current density of 10mA / cm ^2, was measured for luminous efficiency and color coordinates, and 95% compared to the initial luminance at a current density of 20mA / cm ² is The time to become (LT95) was measured. The results are shown in Table 1 below.

Example blue
Host blue
Dopant 10 mA / cm ² 20 mA / cm ² Driving voltage
(v) efficiency
(cd / A) Color coordinates
CIEy Conversion efficiency
Cd / A / y life span
(hr, LT95) Example 1 BH-1 BD-2 4.2 5.9 0.1 59.0 272 Example 2 BH-1 BD-3 4.3 6.5 0.1 65.0 220 Example 3 BH-1 BD-6 4.5 6.2 0.1 62.0 184 Example 4 BH-1 BD-8 4.1 4.5 0.09 50.0 176 Example 5 BH-1 BD-11 4.5 5.8 0.1 58.0 181 Example 6 BH-2 BD-13 4.7 5.9 0.11 53.6 160 Example 7 BH-1 + BH-2 BD-2 4.1 6.0 0.1 60 180 Comparative Example 1 BH-1 D-1 4.3 3.5 0.16 21.9 165 Comparative Example 2 BH-1 D-2 4.5 5.8 0.13 44.6 88 Comparative Example 3 BH-1 D-3 3.5 1.1 0.06 18.3 76 Comparative Example 4 BH-1 D-4 3.1 1.8 0.06 30.0 74

From Table 1, it can be confirmed that Examples 1 to 7 using the compound of Formula 1 of the present application have better efficiency and lifespan characteristics than Comparative Examples 1 to 4.

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,
R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Silyl groups; Boron group; Hydroxyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted alkylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylalkylamine group; Substituted or unsubstituted arylheteroarylamine group; Substituted or unsubstituted alkylheteroarylamine group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
Ar1 to Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Silyl groups; Substituted or unsubstituted alkyl group; Substituted or unsubstituted hydrocarbon ring group; Or a substituted or unsubstituted heterocyclic group,
n1 is an integer of 0 to 3, when n1 is 2 or more, two or more R1 are the same as or different from each other,
n2 is an integer of 0 to 5, and when n2 is 2 or more, two or more R2 are the same or different from each other. The method according to claim 1,
Ar 1 to Ar 4 may be the same as or different from each other, and each independently substituted or unsubstituted hydrocarbon ring having 3 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms. The method according to claim 1,
Ar1 to Ar4 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; Substituted or unsubstituted naphthyl group; A substituted or unsubstituted fluorenyl group; Substituted or unsubstituted benzofluorenyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted hydronaphthalene; Substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted carbazole group. The method according to claim 1,
Formula 1 is a compound represented by any one of the following compounds:

. The method according to claim 1,
The compound has a maximum emission peak within 430 nm to 470 nm. A first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound according to any one of claims 1 to 5. . The method according to claim 6,
The organic material layer includes a hole injection layer or a hole transport layer, the hole injection layer or hole transport layer is an organic electronic device comprising the compound. The method according to claim 6,
The organic material layer comprises an electron transport layer or an electron injection layer, the electron transport layer or an electron injection layer is an organic electronic device comprising the compound. The method according to claim 6,
The organic material layer includes an emission layer, and the emission layer includes the compound. The method according to claim 6,
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 6,
The organic electronic device is selected from the group consisting of an organic light emitting device, an organic phosphor, an organic solar cell, an organic photoconductor (OPC) and a glass transistor. The method according to claim 10,
The light emitting layer is an organic electronic device further comprising Formula 1-A as a host:
[Formula 1-A]

In Chemical Formula 1-A,
A1 to A3 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
L1 to L3 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,
R11 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 R11 is same or different from each other. The method according to claim 10,
The light emitting layer is an organic electronic device further comprising at least two of the compounds represented by the general formula 1-B and formula 1-C as a host:
[Formula 1-B]

[Formula 1-C]

In Chemical Formulas 1-B and 1-C,
A4 to A8 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted aryl group,
A9 is a substituted or unsubstituted heterocyclic group,
L4 to L9 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,
R12 and R13 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 parentheses are the same or different from each other.

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