KR20200011027A - Compound and organic light-emitting device comprising the same - Google Patents

Abstract

The present specification relates to a compound of chemical formula 1 and an organic light emitting device comprising the same. The organic light emitting device comprising the compound represented by the chemical formula 1 according to an embodiment of the present specification can have improved efficiency, low driving voltage, and/or lifespan characteristics.

Description

COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE COMPRISING THE SAME

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

This application claims the benefit of the filing date of Korean Patent Application No. 10-2018-0085395 filed with the Korea Patent Office on July 23, 2018, the entire contents of which are incorporated herein.

In order to commercialize the organic light emitting device, it is necessary to improve the efficiency of the light emitting material. For this purpose, studies on phosphorescent and delayed fluorescent materials have been actively conducted. However, in the case of the phosphorescent material, although the high efficiency can be achieved, there is a problem in that the price of the metal complex required to implement phosphorescence is high and the life is short.

In the case of delayed fluorescent materials, a recent concept of thermally activated delayed fluorescence (TADF) was introduced to introduce a high-efficiency green fluorescent material with high external quantum efficiency. The concept of thermal activation delayed fluorescence (TADF) represents a phenomenon in which the reverse energy transfer from an excitation triplet state to an excitation singlet state by thermal activation leads to fluorescence emission, and since the light emission occurs through the triplet, it generally has a long lifetime. It is called delayed fluorescence because long light emission occurs. Since the delayed fluorescent material can use both fluorescence and phosphorescence emission, it can solve the problem of external quantum efficiency of the existing fluorescent material and can solve the price problem of phosphorescent material in that it does not need to include a metal complex.

International Publication No. 2016-015810

Nature, 492, pp 234-238 J. Am. Chem. Soc., 2012, 134 (36), pp 14706-14709

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

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

[Formula 1]

In Chemical Formula 1,

Ar 1 is hydrogen; A substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms,

R1 to R4, R6 and R7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Cyano group; Halogen group; A substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; Substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, or adjacent groups combine with each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms,

R5 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms,

r1, r4, r6 and r7 are each an integer of 1 to 4,

r2 and r3 are each an integer of 1 to 3,

When r1 is 2 or more, the two or more R1 are the same as or different from each other,

When r2 is 2 or more, the two or more R2 are the same as or different from each other,

When r3 is 2 or more, the two or more R3 are the same as or different from each other,

When r4 is 2 or more, the two or more R4s are the same as or different from each other,

When r6 is 2 or more, the two or more R6 are the same as or different from each other,

When r7 is 2 or more, the two or more R7s are the same as or different from each other,

와

는 서로 상이하고,When Ar1 is hydrogen,

Wow

Are different from each other,

는 상기 화학식 1에 결합되는 부위를 의미한다.

Means a site bonded to the formula (1).

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

An organic light emitting device including the compound represented by Formula 1 according to an exemplary embodiment of the present specification may improve efficiency, low driving voltage, and / or lifespan characteristics.

1 and 2 illustrate an organic light emitting device according to an exemplary embodiment of the present specification.
3 is a UV-vis absorption spectrum and photoluminescence spectrum of Compound 3 of Compound 3 according to an exemplary embodiment of the present specification.

Hereinafter, this specification is demonstrated in detail.

An exemplary embodiment of the present specification provides a compound represented by Chemical Formula 1.

According to an exemplary embodiment of the present specification, the compound represented by Formula 1 is a delayed fluorescent compound.

In the present specification, the delayed fluorescence means that the excitons convert from the triplet excited state T1 to the singlet excited state S1 to emit fluorescence in the singlet excited state S1. Delayed fluorescence is distinguished from fluorescence in that the peak position of the emission spectrum is the same as the fluorescence but the decay time is long, and the peak position of the emission spectrum is different by the difference between the phosphorescence spectrum and the S1-T1 energy. Is distinguished from phosphorescence.

Compound represented by Formula 1 according to an exemplary embodiment of the present specification is the two CN is bonded to the meta position based on the phenyl linker, acts as an electron acceptor (acceptor), substituted or unsubstituted carbazole And a substituted or unsubstituted biscarbazole is bonded to each other in a meta position to serve as an electron donor. Thermally activated delayed fluorescence (TADF) is expressed by the charge transfer (CT) characteristics between the electron donor and the electron acceptor. The number of CN bonds in the donor and electron acceptor bound to the electron phenyl linker As it increases, CN bonds become stressed. However, the structure of Formula 1 may introduce a substituted or unsubstituted biscarbazole having a strong electron donating ability, thereby reducing the number of C-N bonds between the electron donor and the electron acceptor. In addition, substituted or unsubstituted carbazole and substituted or unsubstituted biscarbazole are bonded to each other in a meta position, and the distortion of the electron donor can be reduced, so that stability of the bond can be expected. Therefore, the organic light emitting device including the same may improve efficiency, low driving voltage, and / or lifespan characteristics.

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

In the present specification, when a part "includes" a certain component, this means that the component may further include other components, except for the case where there is no description to the contrary.

은 치환기에 연결되는 위치를 말한다.In this specification,

Refers to a position linked to a substituent.

Examples of substituents in the present specification 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 substituted, that is, a position where a substituent can be substituted, if two or more 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; Substituted or unsubstituted alkyl 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 heteroaryl group, or two or more substituents in the substituents exemplified above are substituted, 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.

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

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 50 carbon atoms, more preferably 1 to 30 carbon atoms. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl, and the like, but is not limited thereto.

In the present specification, the aryl group may be a monocyclic aryl group or a polycyclic aryl group.

In the present specification, when the aryl group is a monocyclic aryl group, carbon number is not particularly limited, but is preferably 6 to 50 carbon atoms, more preferably 6 to 30 carbon atoms. Specifically, monocyclic aryl groups include, but are not limited to, phenyl groups, biphenyl groups, terphenyl groups, quarterphenyl groups, and the like.

In the present specification, when the aryl group is a polycyclic aryl group, carbon number is not particularly limited. It is preferable that it is C10-C50, and it is more preferable that it is C10-C30. Specifically, examples of the polycyclic aryl group include naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but are not limited thereto.

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

,

,

,

,

,

등이 될 수 있으나, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

,

,

,

,

Etc., but is not limited thereto.

In the present specification, the term "adjacent" means a substituent substituted on an atom directly connected to the atom to which the corresponding substituent is substituted, a substituent positioned closest to the substituent, or another substituent substituted on the atom to which the substituent is substituted. Can be. For example, two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as "adjacent" groups.

In the present specification, the heteroaryl group includes one or more of N, O, S, Si, and Se as hetero atoms, and the carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms, and more preferably 2 to 30 carbon atoms. desirable. Examples of the heteroaryl group include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, acri Din group, pyridazine group, pyrazine group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidine group, pyrido pyrazine group, pyrazino pyrazine group, isoquinoline group, indole group, carba Drowsiness, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuran group, phenanthridine group, phenanthridine group, phenanthroline group, phentriol group A pteridine, thiazolyl group, isooxazolyl group, oxadiazolyl group, thiadiazolyl group, and dibenzofuran group, but are not limited thereto.

In the present specification, the heterocyclic group may be selected from the examples of the heteroaryl group except for an aliphatic, aromatic, or a condensed ring of aliphatic and aromatic, but is not limited thereto.

In the present specification, the arylene group refers to a divalent group having two bonding positions in the aryl group. The description of the aforementioned aryl groups can be applied except that they are each divalent.

In the present specification, a heteroarylene group means a divalent group having two bonding positions in an aryl group. The description of the heteroaryl group described above can be applied except that they are each divalent.

In the present specification, in a substituted or unsubstituted ring in which adjacent groups are bonded to each other, a “ring” means a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted hetero ring.

In the present specification, the aromatic hydrocarbon ring may be monocyclic or polycyclic, and may be selected from examples of the aryl group except that it is not monovalent.

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

According to an exemplary embodiment of the present specification, in the general formula 1, Ar1 is hydrogen.

According to an exemplary embodiment of the present specification, in the general formula 1, Ar1 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

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

[Formula 1-1]

[Formula 1-2]

In Chemical Formulas 1-1 and 1-2,

Ar11 is a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms,

Definitions of R1 to R7, r1 to r4, r6 and r7 are the same as defined in the formula (1).

According to an exemplary embodiment of the present specification, in the general formula 1, R5 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, in the general formula 1, R5 is a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, in the general formula 1, R5 is a monocyclic or polycyclic aryl group having 6 to 12 carbon atoms.

According to an exemplary embodiment of the present specification, in the general formula 1, R5 is a phenyl group; Biphenyl group; Or a naphthyl group.

According to an exemplary embodiment of the present specification, in the general formula 1, R1 to R4, R6 and R7 are the same as or different from each other, and each independently hydrogen; Linear or branched alkyl groups having 1 to 30 carbon atoms; Monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms; Or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or adjacent groups are bonded to each other to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms do.

According to an exemplary embodiment of the present specification, in the general formula 1, R1 to R4, R6 and R7 are the same as or different from each other, and each independently hydrogen; Linear or branched alkyl groups having 1 to 20 carbon atoms; Monocyclic or polycyclic aryl groups having 6 to 20 carbon atoms; Or a C2-C20 monocyclic or polycyclic heteroaryl group unsubstituted or substituted with a C6-C20 monocyclic or polycyclic aryl group, or adjacent groups combine with each other to form a C6-C20 monocyclic or polycyclic aromatic hydrocarbon ring do.

According to an exemplary embodiment of the present specification, in the general formula 1, R1 to R4, R6 and R7 are the same as or different from each other, and each independently hydrogen; Linear or branched alkyl groups having 1 to 10 carbon atoms; Monocyclic or polycyclic aryl groups having 6 to 10 carbon atoms; Or a C2-C12 monocyclic or polycyclic heteroaryl group substituted or unsubstituted with a C6-C10 monocyclic or polycyclic aryl group, or adjacent groups combine with each other to form a C6-C10 monocyclic or polycyclic aromatic hydrocarbon ring do.

According to an exemplary embodiment of the present specification, in the general formula 1, R1 to R4, R6 and R7 are the same as or different from each other, and each independently hydrogen; Methyl group; Phenyl group; Or a carbazole group unsubstituted or substituted with a phenyl group, or adjacent groups form a benzene ring with each other.

According to an exemplary embodiment of the present specification, in the general formula 1, R2, R3 and R4 are the same as or different from each other, and each independently hydrogen; Or deuterium.

According to an exemplary embodiment of the present specification, in the general formula 1, R2, R3 and R4 is hydrogen.

According to an exemplary embodiment of the present specification, in the general formula 1, R1, R6 and R7 are the same as or different from each other, and each independently hydrogen; Linear or branched alkyl groups having 1 to 30 carbon atoms; Monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms; Or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or adjacent groups are bonded to each other to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms do.

According to an exemplary embodiment of the present specification, in the general formula 1, R1, R6 and R7 are the same as or different from each other, and each independently hydrogen; Linear or branched alkyl groups having 1 to 20 carbon atoms; Monocyclic or polycyclic aryl groups having 6 to 20 carbon atoms; Or a C2-C20 monocyclic or polycyclic heteroaryl group unsubstituted or substituted with a C6-C20 monocyclic or polycyclic aryl group, or adjacent groups combine with each other to form a C6-C20 monocyclic or polycyclic aromatic hydrocarbon ring do.

According to an exemplary embodiment of the present specification, in the general formula 1, R1, R6 and R7 are the same as or different from each other, and each independently hydrogen; Linear or branched alkyl groups having 1 to 10 carbon atoms; Monocyclic or polycyclic aryl groups having 6 to 10 carbon atoms; Or a C2-C12 monocyclic or polycyclic heteroaryl group substituted or unsubstituted with a C6-C10 monocyclic or polycyclic aryl group, or adjacent groups combine with each other to form a C6-C10 monocyclic or polycyclic aromatic hydrocarbon ring do.

According to an exemplary embodiment of the present specification, in the general formula 1, R1, R6 and R7 are the same as or different from each other, and each independently hydrogen; Methyl group; Phenyl group; Or a carbazole group unsubstituted or substituted with a phenyl group, or adjacent groups form a benzene ring with each other.

According to an exemplary embodiment of the present specification, in the general formula 1, R1 is hydrogen; Or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, in the general formula 1, R1 is hydrogen; Or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, in the general formula 1, R1 is hydrogen; Or a monocyclic or polycyclic heteroaryl group having 2 to 12 carbon atoms which is unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, in the general formula 1, R1 is hydrogen; Or a carbazole group substituted with a phenyl group.

According to an exemplary embodiment of the present specification, in the general formula 1, R6 is hydrogen; Linear or branched alkyl groups having 1 to 30 carbon atoms; Monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms; Or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or adjacent groups are bonded to each other to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms do.

According to an exemplary embodiment of the present specification, in the general formula 1, R6 is hydrogen; Linear or branched alkyl groups having 1 to 20 carbon atoms; Monocyclic or polycyclic aryl groups having 6 to 20 carbon atoms; Or a C2-C20 monocyclic or polycyclic heteroaryl group unsubstituted or substituted with a C6-C20 monocyclic or polycyclic aryl group, or adjacent groups combine with each other to form a C6-C20 monocyclic or polycyclic aromatic hydrocarbon ring do.

According to an exemplary embodiment of the present specification, in the general formula 1, R6 is hydrogen; Linear or branched alkyl groups having 1 to 10 carbon atoms; Monocyclic or polycyclic aryl groups having 6 to 10 carbon atoms; Or a C2-C12 monocyclic or polycyclic heteroaryl group substituted or unsubstituted with a C6-C10 monocyclic or polycyclic aryl group, or adjacent groups combine with each other to form a C6-C10 monocyclic or polycyclic aromatic hydrocarbon ring do.

According to an exemplary embodiment of the present specification, in the general formula 1, R6 is hydrogen; Methyl group; Phenyl group; Or a carbazole group unsubstituted or substituted with a phenyl group, or adjacent groups form a benzene ring with each other.

According to an exemplary embodiment of the present specification, in the general formula 1, R6 is hydrogen; Methyl group; Or a carbazole group unsubstituted or substituted with a phenyl group, or adjacent groups form a benzene ring with each other.

이거나, 인접한 기는 서로 벤젠 고리를 형성한다.According to an exemplary embodiment of the present specification, in the general formula 1, R6 is hydrogen; Methyl group; or

Or adjacent groups form a benzene ring with one another.

이거나, 인접한 기는 서로 벤젠 고리를 형성한다.According to an exemplary embodiment of the present specification, in the general formula 1, R6 is hydrogen; An alkyl group having 1 to 6 carbon atoms; Aryl groups having 6 to 20 carbon atoms; or

Or adjacent groups form a benzene ring with one another.

이거나, 인접한 기는 서로 벤젠 고리를 형성한다.According to an exemplary embodiment of the present specification, in the general formula 1, R6 is hydrogen; Methyl group; Phenyl group; or

Or adjacent groups form a benzene ring with one another.

According to an exemplary embodiment of the present specification, in the general formula 1, R6 is hydrogen; Methyl group; Or a phenyl group, or adjacent groups form a benzene ring with one another.

According to an exemplary embodiment of the present specification, in the general formula 1, R7 is hydrogen; Linear or branched alkyl groups having 1 to 30 carbon atoms; Monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms; Or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or adjacent groups are bonded to each other to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms do.

According to an exemplary embodiment of the present specification, in the general formula 1, R7 is hydrogen; Linear or branched alkyl groups having 1 to 20 carbon atoms; Monocyclic or polycyclic aryl groups having 6 to 20 carbon atoms; Or a C2-C20 monocyclic or polycyclic heteroaryl group unsubstituted or substituted with a C6-C20 monocyclic or polycyclic aryl group, or adjacent groups combine with each other to form a C6-C20 monocyclic or polycyclic aromatic hydrocarbon ring do.

According to an exemplary embodiment of the present specification, in the general formula 1, R7 is hydrogen; Linear or branched alkyl groups having 1 to 10 carbon atoms; Monocyclic or polycyclic aryl groups having 6 to 10 carbon atoms; Or a C2-C12 monocyclic or polycyclic heteroaryl group substituted or unsubstituted with a C6-C10 monocyclic or polycyclic aryl group, or adjacent groups combine with each other to form a C6-C10 monocyclic or polycyclic aromatic hydrocarbon ring do.

According to an exemplary embodiment of the present specification, in the general formula 1, R7 is hydrogen; Methyl group; Phenyl group; Or a carbazole group unsubstituted or substituted with a phenyl group, or adjacent groups form a benzene ring with each other.

According to an exemplary embodiment of the present specification, in the general formula 1, R7 is hydrogen; Methyl group; Or a carbazole group unsubstituted or substituted with a phenyl group, or adjacent groups form a benzene ring with each other.

이거나, 인접한 기는 서로 벤젠 고리를 형성한다.According to an exemplary embodiment of the present specification, in the general formula 1, R7 is hydrogen; Methyl group; or

Or adjacent groups form a benzene ring with one another.

이거나, 인접한 기는 서로 벤젠 고리를 형성한다.According to an exemplary embodiment of the present specification, in the general formula 1, R7 is hydrogen; An alkyl group having 1 to 6 carbon atoms; Aryl groups having 6 to 20 carbon atoms; or

Or adjacent groups form a benzene ring with one another.

이거나, 인접한 기는 서로 벤젠 고리를 형성한다.According to an exemplary embodiment of the present specification, in the general formula 1, R7 is hydrogen; Methyl group; Phenyl group; or

Or adjacent groups form a benzene ring with one another.

According to an exemplary embodiment of the present specification, in the general formula 1, R7 is hydrogen; Methyl group; Or a phenyl group, or adjacent groups form a benzene ring with one another.

According to an exemplary embodiment of the present specification, in the general formula 1, Ar1 is hydrogen; Linear or branched alkyl groups having 1 to 30 carbon atoms; Or a monocyclic or polycyclic allyl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, in the general formula 1, Ar1 is hydrogen; Linear or branched alkyl groups having 1 to 20 carbon atoms; Or a monocyclic or polycyclic allyl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, in the general formula 1, Ar1 is hydrogen; Linear or branched alkyl groups having 1 to 10 carbon atoms; Or a monocyclic or polycyclic allyl group having 6 to 15 carbon atoms.

According to an exemplary embodiment of the present specification, in the general formula 1, Ar1 is hydrogen; Linear or branched alkyl groups having 1 to 5 carbon atoms; Or a monocyclic or polycyclic allyl group having 6 to 12 carbon atoms.

According to an exemplary embodiment of the present specification, in the general formula 1, Ar1 is hydrogen; Methyl group; Ethyl group; t-butyl group; Phenyl group; Biphenyl group; Or a naphthyl group.

According to an exemplary embodiment of the present specification, in the general formula 1, Ar1 is hydrogen; Methyl group; Phenyl group; Or 1-naphthyl group.

According to an exemplary embodiment of the present specification, in the chemical formula 1-2, Ar11 is a methyl group; Ethyl group; t-butyl group; Phenyl group; Biphenyl group; Or a naphthyl group.

According to an exemplary embodiment of the present specification, in the formula 1-2, Ar11 is hydrogen; Methyl group; Phenyl group; Or 1-naphthyl group.

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

According to an exemplary embodiment of the present specification, ΔE _st of the compound represented by Formula 1 is less than 0.3 eV.

When the ΔE _st of the compound represented by Formula 1 is less than 0.3 eV, the transition from the triplet to the singlet occurs efficiently, thereby increasing the external light emission efficiency and lifetime of the device, and when ΔE _st is 0.3eV or more, triple There is a problem in that the transition from the port to the singlet is difficult to occur and the efficiency and lifetime are lowered.

An exemplary embodiment of the present specification provides an organic light emitting device including the compound.

According to an exemplary embodiment of the present specification, the first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including at least one organic material layer including a light emitting layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound described above. .

According to an exemplary embodiment of the present specification, the organic material layer of the organic light emitting device of the present specification may be formed of a single layer structure, but may be formed of a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer and the like as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include fewer or more organic layers.

For example, the structure of the organic light emitting device of the present specification may have a structure as shown in FIG. 1, but is not limited thereto.

1 illustrates a structure of an organic light emitting device 10 in which a first electrode 30, a light emitting layer 40, and a second electrode 50 are sequentially stacked on a substrate 20. 1 is a compound represented by Formula 1 according to an exemplary embodiment of the present specification may be included in the light emitting layer 40.

2 illustrates a first electrode 30, a hole injection layer 60, a hole transport layer 70, an electron blocking layer 80, a light emitting layer 40, a hole blocking layer 90, an electron injection layer on a substrate 20. The structure of the organic light emitting device 10 in which the transport layer 100 and the second electrode 50 are sequentially stacked is illustrated. The compound represented by Chemical Formula 1 according to one embodiment of the present specification may be included in the light emitting layer 40.

1 and 2 are exemplary structures of the organic light emitting device according to the exemplary embodiment of the present specification, and may further include other organic material layers.

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

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

According to an exemplary embodiment of the present specification, the maximum emission wavelength of the dopant is 450nm to 650nm, specifically 480nm to 550nm.

According to an exemplary embodiment of the present specification, the light emitting material of the light emitting layer is a material capable of emitting light in the visible light region by transporting and bonding holes and electrons from the hole transporting layer and the electron transporting layer, respectively, wherein the light emitting layer is a light emitting layer As a dopant, wherein at least one of the singlet excitation energy and the excitation triplet energy has a higher value than the light emitting material of the compound, has a hole transporting ability, an electron transporting ability, and prevents the long wavelength of luminescence, Organic compounds having a high glass transition temperature may be included as hosts.

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

According to the exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes any one or more selected from a condensed aromatic ring derivative and a heterocyclic containing compound as a host of the light emitting layer.

According to an exemplary embodiment of the present specification, the condensed aromatic ring derivative includes an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound, and the heterocyclic-containing compound as a carbazole derivative. , Dibenzofuran derivatives, ladder type furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

According to an exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, the light emitting layer includes the compound as a dopant of the light emitting layer, and includes any one or more selected from formulas A to F as a host of the light emitting layer.

[Formula A]

In Chemical Formula A,

Y11 is NR ', S or O,

q1 is an integer of 0 to 3,

R 'is a straight or branched chain alkyl group having 1 to 30 carbon atoms; Or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms,

[Formula B]

In Chemical Formula B,

Y12 is O or S,

L1 is a biphenylylene group; Fluorenylene groups unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a spirobifluorenylene group,

A1 is a silyl group substituted with a straight or branched chain alkyl group having 1 to 30 carbon atoms, a straight or branched chain alkyl group having 1 to 30 carbon atoms, or a carbazole group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms Is,

[Formula C]

In Chemical Formula C,

Q1 to Q8 are the same as or different from each other, and each independently hydrogen; Monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with a heteroaryl group having 2 to 30 carbon atoms; Or a heteroaryl group having 2 to 30 carbon atoms, or adjacent groups are bonded to each other to form a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a monocyclic group having 2 to 30 carbon atoms unsubstituted or substituted with a heteroaryl group having 2 to 30 carbon atoms. To form a heterocycle of the ring,

[Formula D]

[Formula E]

In Chemical Formulas D and E,

Y13 and Y14 are the same as or different from each other, and each independently O or S,

Z1 to Z6 are the same as or different from each other, and each independently N or CR ",

L2 and L3 are the same as or different from each other, and each independently a direct bond; Monocyclic or polycyclic arylene groups having 6 to 30 carbon atoms; Or a monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms,

A2 and A3 are the same as or different from each other, and each independently cyano group; Substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms,

R ″ and G1 to G4 are the same as or different from each other, and each independently hydrogen; deuterium; cyano group; halogen group; substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; substituted or unsubstituted carbon number 6 Or a monocyclic or polycyclic aryl group of 30 to 30, or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, or adjacent groups combine with each other to form a substituted or unsubstituted ring,

g1 and g3 are each an integer of 1 to 7,

g2 is an integer of 1 to 3,

g4 is an integer of 1 to 8,

When g1 is 2 or more, the two or more G1 are the same as or different from each other,

When g2 is 2 or more, the two or more G2s are the same as or different from each other,

When g3 is 2 or more, the two or more G3 are the same as or different from each other,

When g4 is 2 or more, the two or more G4 are the same as or different from each other,

Formula F]

In Chemical Formula F,

L13 is a substituted or unsubstituted (b + 1) valent aryl group; Or a (b + 1) valent heteroaryl group,

G11 and G12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Cyano group; Or a heteroaryl group containing O or S,

b13 is an integer of 1 to 3, when b13 is 2 or more, L13 is the same as or different from each other,

는 서로 같거나 상이하다.b is 1 or 2, if b is 2

Are the same as or different from each other.

According to an exemplary embodiment of the present specification, the light emitting layer includes the dopant and the host in a weight ratio of 1:99 to 50:50.

According to an exemplary embodiment of the present specification, the light emitting layer includes the dopant and the host in a weight ratio of 20:80 to 50:50.

Within this range, energy transfer from the host to the dopant occurs efficiently.

According to an exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes a dopant including the compound described above and a host including any one or more selected from Formulas A to F: 1:99 to 50: It is included in the weight ratio of 50.

According to an exemplary embodiment of the present specification, the formula A is selected from the following compounds.

According to an exemplary embodiment of the present specification, in the general formula B, L1 is any one selected from the following structures.

According to an exemplary embodiment of the present specification, in the general formula B, A1 is represented by the following structure.

In the above structure,

A2 and A3 are the same as or different from each other, and each independently hydrogen; Alkyl groups; Silyl groups substituted with alkyl groups; Or an aryl group,

o and p are each an integer of 1 to 4,

When o and p are each 2 or more, the structures in the two or more parentheses are the same as or different from each other.

According to yet an embodiment of the present disclosure, the A2 and A3 are the same as or different from each other, and each independently hydrogen; Methyl group; t-butyl group; Trimethylsilyl group; Phenyl group; Or a biphenyl group.

According to an exemplary embodiment of the present specification, in the general formula C, Q1 to Q8 are the same as or different from each other, and each independently hydrogen; A phenyl group unsubstituted or substituted with a carbazolyl group or a dibenzofuran group; Biphenyl group; Terphenyl group; Or a carbazole group.

According to an exemplary embodiment of the present specification, in the general formula C, adjacent groups of Q1 to Q8 are bonded to each other to form a benzofuran ring unsubstituted or substituted with an aryl group or a heteroaryl group.

According to an exemplary embodiment of the present specification, in the general formula C, adjacent groups of Q1 to Q8 combine with each other to form a benzofuran ring unsubstituted or substituted with a biphenyl group, a terphenyl group, or a carbazole group.

According to an exemplary embodiment of the present specification, the formula C is selected from the following compounds.

According to an exemplary embodiment of the present disclosure, wherein R "is hydrogen.

According to an exemplary embodiment of the present specification, in the general formula D, G1 to G3 are the same as or different from each other, and each independently hydrogen; Cyano group; Monocyclic or polycyclic heteroaryl groups having 2 to 30 carbon atoms, or adjacent groups combine with each other to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present specification, in the general formula D, G1 to G3 are the same as or different from each other, and each independently hydrogen; Cyano group; Monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms; A monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, or adjacent groups are bonded to each other and substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms or a linear or branched alkyl group having 1 to 30 carbon atoms To form.

According to an exemplary embodiment of the present specification, in the general formula D, G1 to G3 are the same as or different from each other, and each independently hydrogen; Cyano group; Phenyl group; A carbazole group, or an adjacent group in which an adjacent group is bonded to each other and substituted or unsubstituted with a phenyl group; Benzothiophene ring; Benzofuran ring; Or a substituted or unsubstituted indene ring with a methyl group.

According to an exemplary embodiment of the present specification, in the general formula D, G2 and G3 is hydrogen.

According to an exemplary embodiment of the present specification, in the general formula D, G1 is hydrogen; Cyano group; Monocyclic or polycyclic heteroaryl groups having 2 to 30 carbon atoms, or adjacent groups combine with each other to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present specification, in the general formula D, G1 is hydrogen; Cyano group; Monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms; A monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, or adjacent groups are bonded to each other and substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms or a linear or branched alkyl group having 1 to 30 carbon atoms To form.

According to an exemplary embodiment of the present specification, in the general formula D, G1 is hydrogen; Cyano group; Phenyl group; A carbazole group, or an adjacent group in which an adjacent group is bonded to each other and substituted or unsubstituted with a phenyl group; Benzothiophene ring; Benzofuran ring; Or a substituted or unsubstituted indene ring with a methyl group.

According to an exemplary embodiment of the present specification, the formula D is selected from the following compounds.

According to an exemplary embodiment of the present specification, in the general formula E, G4 is hydrogen.

According to an exemplary embodiment of the present specification, in the formula E, L2 and L3 are the same as or different from each other, and each independently a direct bond; Phenylene group; Divalent dibenzofuran group; Or a divalent dibenzothiophene group.

According to an exemplary embodiment of the present specification, in the general formula E, A2 and A3 are the same as or different from each other, and each independently a cyano group; Monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms; Or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, in the general formula E, A2 and A3 are the same as or different from each other, and each independently a cyano group; Phenyl group; Dibenzofuran group unsubstituted or substituted with a phenyl group; Dibenzothiophene group unsubstituted or substituted with a phenyl group; Or a triazine group unsubstituted or substituted with a phenyl group.

According to an exemplary embodiment of the present specification, the formula E is selected from the following compounds.

In an exemplary embodiment of the present specification, in the general formula F, L13 is a substituted or unsubstituted (b + 1) valent aryl group having 6 to 16 carbon atoms; Or a (b + 1) valent heteroaryl group having 2 to 16 carbon atoms.

In an exemplary embodiment of the present specification, in the formula F, L13 is a substituted or unsubstituted (b + 1) valent aryl group having 6 to 12 carbon atoms; Or a heteroaryl group having 2 to 12 carbon atoms (b + 1).

In one embodiment of the present specification, in the general formula F, L13 is a substituted or unsubstituted (b + 1) valent phenyl group; A substituted or unsubstituted (b + 1) valent biphenyl group; (b + 1) valent dibenzofuranyl group; Or a (b + 1) valent pyridinyl group.

In an exemplary embodiment of the present specification, in the general formula F, when L13 is a substituted (b + 1) valent aryl group, the substituent of the (b + 1) valent aryl group is an aryl group substituted with a heteroaryl group.

In one embodiment of the present specification, in the general formula F, G11 and G12 are the same as or different from each other, and each independently hydrogen; Or cyano group.

In one embodiment of the present specification, in the general formula F, b13 is 1.

In one embodiment of the present specification, in the general formula F, b13 is 2.

In one embodiment of the present specification, the compound represented by Formula F is any one selected from the following compounds.

According to an exemplary embodiment of the present specification, the organic material layer may include a light emitting layer, and the light emitting layer may further include a fluorescent emitter.

When the fluorescent emitter is included in the emission layer, the fluorescent emitter and the host are included in a weight ratio of 0.5: 99.5 to 10:90.

In the present specification, the fluorescent emitter may be an anthracene-based compound, a pyrene-based compound, a boron-based compound, or the like, but is not limited thereto.

The organic light emitting device of the present specification may be manufactured by materials and methods known in the art, except for including the compound of the present specification, that is, the compound represented by Chemical Formula 1, as a dopant of the emission layer.

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

For example, the organic light emitting device of the present specification may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a physical vapor deposition (PVD: physical vapor deposition) such as sputtering (e-beam evaporation), by depositing a metal or conductive metal oxide or alloys thereof on the substrate It can be prepared by forming a first electrode, forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, and then depositing a material that can be used as a second electrode thereon. In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing a second electrode material, an organic material layer, and a first electrode material on a substrate. In addition, the heterocyclic compound represented by Chemical Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device. Here, the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.

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

According to yet an embodiment of the present disclosure, the first electrode is a cathode, the second electrode is an anode.

As the first electrode material, a material having a large work function is generally preferred to facilitate hole injection into the organic material layer. Specific examples of the first 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), indium zinc oxide (IZO); ZnO: Al or SnO ₂ : Combination of metals and oxides such as 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.

It is preferable that the second electrode material is a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the cathode materials 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, Mg / Ag, and the like, but are not limited thereto.

The hole injection layer is a layer for injecting holes from an electrode with a hole injection material, and has a capability of transporting holes with a hole injection material, and has an excellent hole injection effect at an anode, and an excellent hole injection effect with respect to a light emitting layer or a light emitting material. The compound which prevents the movement of the excitons produced | generated in the light emitting layer to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable. Preferably, the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based Organic materials, anthraquinone and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

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

The electron blocking layer is a layer which can prevent the electrons injected from the electron injection layer from passing through the light emitting layer to the hole injection layer to improve the life and efficiency of the device, and if necessary, using a known material using a known material It may be formed in a suitable portion between injection layers.

When the organic light emitting device includes an additional light emitting layer other than the light emitting layer including the compound represented by Chemical Formula 1, the light emitting material receives light and visible light in the visible region by transporting and combining holes and electrons from the hole transporting layer and the electron transporting layer, respectively. As the substance which can be produced, a substance 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-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene; Or rubrene and the like, but is not limited thereto.

The light emitting layer may include a host material and a dopant material. The host material may be a condensed aromatic ring derivative or a hetero ring-containing compound. 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.

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

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. As an electron transporting material, a material capable of injecting electrons well from the cathode and transferring the electrons to the light emitting layer is suitable. Do. Specific examples thereof 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 electron transport layer can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, followed by aluminum layers or silver layers in each case.

The electron injection layer is a layer that injects electrons from an electrode, has an ability of transporting electrons, has an electron injection effect from a cathode, an electron injection effect with respect to a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer The compound which prevents the movement to a layer and 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 five-membered ring derivatives, and the like, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, etc. It is not limited to this.

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

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

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

Production Example

Production Example  1. Preparation of Compound 1

1,5-Dibromo-2,4-difluorobenzene (10 g, 37.06 mmol) was completely dissolved in 110 ml of dimethylformamide, and stirred with increasing temperature until reflux. When it began to reflux, copper cyanide (6.6 g, 74.11 mmol) was slowly added thereto, and after 6 hours, the reaction was completed. The temperature was lowered to room temperature, concentrated under reduced pressure, and column purified to obtain 4.31 g (yield 71%) of intermediate 1-1. It was.

The intermediate 1-1 (4.31 g, 26.31 mmol), 9H-carbazole (4.4 g, 26.31 mmol) and sodium hydride (0.7 g, 28.94 mmol) were added to 90 ml of dimethylformamide, and the mixture was heated and stirred. After 10 hours, the reaction was completed, the temperature was lowered to room temperature, concentrated under reduced pressure, and column purified to obtain 5.24 g (yield 64%) of intermediate 1-2.

Intermediate 1-2 (5.24 g, 16.84 mmol), 9-phenyl-9H, 9'H-3,3'-bicarbazole (6.87 g, 16.84 mmol) and sodium hydride (0.44 g, 18.52 mmol) It is put in 50 ml of dimethylformamide and heated up and stirred. After completion of the reaction for 10 hours, the temperature was lowered to room temperature, concentrated under reduced pressure, and purified by column to obtain 8.01 g (yield 68%) of compound 1.

 MS [M + H] + = 700

Production Example  2. Preparation of Compound 2

4,6-difluoroisonaphthalonitrile (10 g, 60.97 mmol), 5H-benzo [b] carbazole (13.24 g, 60.97 mmol) and sodium hydride (1.61 g, 67.06 mmol) were added to 180 ml of dimethylformamide. The mixture is heated and stirred. After 8 hours, the reaction was completed, the temperature was lowered to room temperature, concentrated under reduced pressure, and column purified to obtain 14.53 g (66% yield) of intermediate 2-1.

The intermediate 2-1 (14.53g, 40.24mmol), 9-phenyl-9H, 9'H-3,3'-bicarbazole (16.42g, 40.24mmol) and sodium hydride (1.06g, 44.26mmol) It is put into dimethylformamide 120ml and the temperature is raised and stirred. After 10 hours, the reaction was completed, the temperature was lowered to room temperature, concentrated under reduced pressure, and column purified to obtain 21.11 g (yield 70%) of compound 2.

 MS [M + H] + = 750

Production Example  3. Preparation of Compound 3

Intermediate 1-2 (10 g, 32.14 mmol), 9,9 ''-diphenyl-9H, 9'H, 9''H-3,3 ': 6', 3 ''-tercarbazole (20.87 g , 32.14 mmol) and sodium hydride (0.85 g, 35.38 mmol) were added to 90 ml of dimethylformamide, and the mixture was heated and stirred. After 13 hours, the reaction was completed, the temperature was lowered to room temperature, concentrated under reduced pressure, and column purified to obtain 17.53 g (yield 58%) of compound 3.

 MS [M + H] + = 941

Production Example  4. Preparation of Compound 4

2,4-Dibromo-1,5-difluoro-3-methylbenzene (10 g, 35.23 mmol) was completely dissolved in 100 ml of dimethylformamide and stirred with increasing temperature until reflux. When it began to reflux, copper cyanide (6.27g, 70.46mmol) was slowly added thereto, and after 5 hours, the reaction was completed, the temperature was lowered to room temperature, concentrated under reduced pressure, and column purified to obtain 4.58 g (yield 73%) of intermediate 4-1. It was.

The intermediate 4-1 (4.58g, 25.73mmol), 9-phenyl-9H, 9'H-3,3'-bicarbazole (21.0g, 51.45mmol) and sodium hydride (1.36g, 56.61mmol) It is put into 80 ml of dimethylformamide and the temperature is raised and stirred. After 14 hours, the reaction was completed, the temperature was lowered to room temperature, concentrated under reduced pressure, and column purified to obtain 16.94 g (yield 69%) of compound 4.

MS [M + H] + = 955

Production Example  5. Preparation of Compound 5

2,4-Dibromo-3-chloro-1,5-difluorobenzene (10 g, 32.92 mmol) was completely dissolved in 90 ml of dimethylformamide and stirred while raising the temperature to reflux. When refluxed, copper cyanide (5.86 g, 65.84 mmol) was slowly added thereto, and after 2 hours, the reaction was completed. The temperature was lowered to room temperature, concentrated under reduced pressure, and column purified to obtain 4.24 g (yield 65%) of intermediate 5-1. It was.

The intermediate 5-1 (4.24g, 21.40mmol), 9H-3,9'-bicarbazole (7.11g, 21.40mmol) and sodium hydride (0.56g, 23.54mmol) were added to 60ml of dimethylformamide and heated up. Stir. After 10 hours, the reaction was completed, the temperature was lowered to room temperature, concentrated under reduced pressure, and column purified to obtain 7.86 g (yield 72%) of intermediate 5-2.

Intermediate 5-2 (7.86 g, 15.41 mmol), 9-phenyl-9H, 9'H-3,3'-bicarbazole (6.29 g, 15.41 mmol) and sodium hydride (0.41 g, 16.95 mmol) It is put in 50 ml of dimethylformamide and heated up and stirred. After 8 hours, the reaction was completed, the temperature was lowered to room temperature, concentrated under reduced pressure, and column purified to obtain 9.14 g (yield 66%) of intermediate 5-3.

The intermediate 5-3 (9.14 g, 10.17 mmol), phenylboronic acid (1.49 g, 12.20 mmol) and 2 mol% of tetrakis (triphenylphosphine) palladium (0) were added to 30 ml of tetrahydrofuran and potassium carbonate (4.22 g). , 30.51 mmol) was mixed with the aqueous solution and the temperature was increased until reflux. After refluxing, the reaction was terminated after 6 hours to lower the temperature to room temperature, concentrated under reduced pressure, and purified by column to obtain 5.55 g (yield 58%) of compound 5.

MS [M + H] + = 941

Production Example  6. Preparation of Compound 6

The intermediate 5-3 (10 g, 11.13 mmol), naphthalen-1-ylboronic acid (1.90 g, 11.13 mmol) and 2 mol% of tetrakis (triphenylphosphine) palladium (0) were added to 30 ml of tetrahydrofuran and potassium carbonate ( 4.60 g, 33.39 mmol) was mixed with an aqueous solution, and the temperature was increased until reflux. After refluxing, the reaction was completed after 5 hours to lower the temperature to room temperature, concentrated under reduced pressure, and purified by column to obtain 6.40 g (yield 58%) of compound 6.

MS [M + H] + = 991

Production Example  7. Preparation of Compound 7

2-chloro-4,6-difluoroisonaphthalonitrile (10g, 50.51mmol), 3,6-dimethyl-9H-carbazole (9.85g, 50.51mmol) and sodium hydride (1.33g, 55.56mmol) To 150 ml of dimethylformamide was added and stirred by heating. After 7 hours, the reaction was completed, the temperature was lowered to room temperature, concentrated under reduced pressure, and column purified to obtain 12.06 g (yield 64%) of intermediate 7-1.

Intermediate 7-1 (12.06 g, 32.33 mmol), 9,9 ''-diphenyl-9H, 9'H, 9''H-3,3 ': 6', 3 ''-tercarbazole (20.99 g, 32.33 mmol) and sodium hydride (0.85 g, 35.56 mmol) were added to 90 ml of dimethylformamide, and the mixture was heated and stirred. After 8 hours, the reaction was completed, the temperature was lowered to room temperature, concentrated under reduced pressure, and column purified to obtain 18.47 g (yield 57%) of intermediate 7-2.

The intermediate 7-2 (18.47 g. 18.43 mmol), phenyl boronic acid (2.25 g, 18.43 mmol) and 2 mol% of tetrakis (triphenylphosphine) palladium (0) were added to 60 ml of tetrahydrofuran and potassium carbonate (7.64 g). , 55.29 mmol) was mixed with the aqueous solution, and the temperature was increased until reflux. 7 hours after the start of reflux, the reaction was terminated to lower the temperature to room temperature, concentrated under reduced pressure, and purified by column to obtain 12.32 g (yield 64%) of compound 7.

MS [M + H] + = 1045

Example 1

Experimental Example 1-1

In the present experimental example, the organic light emitting device was manufactured by including Formula 1 according to an exemplary embodiment of the present specification in a light emitting layer together with a host material (m-CBP) having a triplet value of 2.5 eV or more, and evaluating characteristics thereof.

A glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 Å was placed in distilled water in which detergent was dissolved and ultrasonically cleaned. At this time, Fischer Co. product was used as a detergent, and distilled water filtered secondly as a filter of Millipore Co. product was used as distilled water. After ITO was washed for 30 minutes, ultrasonic washing was performed twice with distilled water for 10 minutes. After washing the distilled water, ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol, dried and transported to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator. Each thin film was laminated on the thus prepared ITO transparent electrode with a vacuum degree of 5.0 Х 10 ⁻⁴ Pa by vacuum deposition.

First, hexanitrile hexaazatriphenylene (HAT) was thermally vacuum deposited to a thickness of 500 kPa on ITO to form a hole injection layer.

Compound 4-4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPB) (300 Pa), which is a substance for transporting holes on the hole injection layer, was vacuum deposited to form a hole transport layer. It was.

The compound N-([1,1'-bisphenyl] -4-yl) -N- (4- (11-([1,1'-biphenyl] -4-yl) has a film thickness of 100 kPa on the hole transport layer. ) -11H-benzo [a] carbazole-5-yl) phenyl)-[1,1'-biphenyl] -4-amine (EB1) (100 Pa) was vacuum deposited to form an electron blocking layer.

Subsequently, the following m-CBP and Compound 1 were vacuum-deposited at a weight ratio of 70:30 on the electron blocking layer with a film thickness of 300 Pa to form a light emitting layer.

Compound HB1 was vacuum deposited on the light emitting layer to have a film thickness of 100 GPa to form a hole blocking layer.

Compound ET1 and compound LiQ (Lithium Quinolate) were vacuum deposited on the hole blocking layer in a weight ratio of 1: 1 to form an electron injection and transport layer at a thickness of 300 kPa. On the electron injection and transport layer, lithium fluoride (LiF) and aluminum were deposited to a thickness of 2,000 kW in order to form a cathode.

Was maintained at the deposition rate was 0.4 ~ 0.7Å / sec for organic material in the above process, the lithium fluoride of the cathode was 0.3Å / sec, aluminum is deposited at a rate of 2Å / sec, During the deposition, a vacuum 2 x 10 ^{- The} organic light emitting device was manufactured by maintaining ⁷ to 5 × 10 ⁻⁶ torr.

<Experimental Example 1-2>

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 2 was used instead of compound 1 in Experimental Example 1-1.

<Experimental Example 1-3>

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 3 was used instead of compound 1 in Experimental Example 1-1.

<Experimental Example 1-4>

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 4 was used instead of compound 1 in Experimental Example 1-1.

<Experimental Example 1-5>

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 5 was used instead of compound 1 in Experimental Example 1-1.

<Experimental Example 1-6>

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 6 was used instead of compound 1 in Experimental Example 1-1.

<Experimental Example 1-7>

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 7 was used instead of compound 1 in Experimental Example 1-1.

<Comparative Example 1-1>

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that TD 1 was used instead of compound 1 in Experimental Example 1-1.

<Comparative Example 1-2>

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that TD 2 was used instead of compound 1 in Experimental Example 1-1.

Comparative Example 1-3

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that TD 3 was used instead of compound 1 in Experimental Example 1-1.

<Comparative Example 1-4>

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that TD 4 was used instead of compound 1 in Experimental Example 1-1.

<Comparative Example 1-5>

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that 4CzIPN was used instead of compound 1 in Experimental Example 1-1.

When the current was applied to the organic light emitting devices manufactured by Experimental Examples 1-1 to 1-7 and Comparative Examples 1-1 to 1-5, the results of Table 1 were obtained.

division compound
(Light emitting layer) Voltage
(V @ 10mA / cm ² ) efficiency
(cd / A @ 10mA / cm ² ) Color coordinates
(x, y) Experimental Example 1-1 Compound 1 3.8 24.7 (0.33, 0.63) Experimental Example 1-2 Compound 2 4.0 23.1 (0.34, 0.62) Experimental Example 1-3 Compound 3 3.7 25.8 (0.33, 0.63) Experimental Example 1-4 Compound 4 4.1 23.9 (0.33, 0.64) Experimental Example 1-5 Compound 5 4.0 23.7 (0.33, 0.62) Experimental Example 1-6 Compound 6 3.9 24.1 (0.32, 0.63) Experimental Example 1-7 Compound 7 3.9 24.0 (0.33, 0.64) Comparative Example 1-1 TD 1 5.1 10.8 (0.25, 0.63) Comparative Example 1-2 TD 2 5.1 11.5 (0.29, 0.58) Comparative Example 1-3 TD 3 4.9 13.8 (0.44, 0.66) Comparative Example 1-4 TD 4 4.8 14.1 (0.53, 0.39) Comparative Example 1-5 4CzIPN 4.7 15.7 (0.31, 0.64)

As shown in Table 1, the devices of Experimental Examples 1-1 to 1-7 using the compound having the structure of Formula 1 has a lower voltage, efficiency than the device using the material of Comparative Examples 1-1 to 1-5 Improved results were obtained.

Compared with 4CzIPN used in Comparative Examples 1-5, the compounds of the present invention can improve the life. TADF is expressed through a CT character between donor-acceptors, and the C-N bond between donor-acceptors is stressed. Therefore, while introducing triscarbazole having a stronger donor strength than carbazole, the number of donors is reduced from four to two, thereby reducing the number of C-N bonds between donor-acceptors.

In addition, compared to 4CzIPN in which carbazole exists as an ortho, the compounds of the present invention have less steric hindrance of donors because the donors exist in meta form, and thus, stability of C-N bond binding can be expected.

As shown in Table 1, the compound according to the present invention was confirmed that the excellent light emitting ability and high color purity can be applied to the delayed fluorescent organic light emitting device.

Example 2

3 is a UV-vis absorption spectrum, a photoluminescence spectrum in a solid state and a photoluminescence spectrum in a low-temperature state, and UV-vis absorption of Compound 3 according to one embodiment of the present specification The spectrum was measured using JASCO's V-730, the absorption spectrum is 200nm to 700nm. HPLC grade tetrahydrofuran (THF) was used as the solvent, and the content of Compound 3 was 10 ^-5 M. Photoluminescence spectra at low temperature (Temperature) state was measured using LS-55 of Perkin Elmer, and the emission spectrum at excitation wavelength of 445nm is 400nm to 700nm. HPLC grade THF was used as the solvent and measured under liquid nitrogen.

Physical properties of the compound 3 according to Figure 3 are shown in Table 2 below.

UV edge (nm) 460 UV gap (eV) 2.70 Fluorescent PL (nm) Onset 444 Max 495 Phosphorescent PL (nm) Onset 464 Max 512 Singlet energy (eV) Onset 2.79 Max 2.51 Triplet energy (eV) Onset 2.67 Max 2.42 S1-T1 (onset) 0.12 0.12

It can be seen that Compound 3, which is one of the examples of the present application, is suitable as a delayed fluorescent compound having ΔEst of 0.2 eV or less.

10: organic light emitting device
20: substrate
30: first electrode
40: light emitting layer
50: second electrode
60: hole injection layer
70: hole transport layer
80: electron blocking layer
90: hole blocking layer
100: electron injection and transport layer

Claims (13)

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

In Chemical Formula 1,
Ar 1 is hydrogen; A substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms,
R1 to R4, R6 and R7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Cyano group; Halogen group; A substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; Substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, or adjacent groups combine with each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms,
R5 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms,
r1, r4, r6 and r7 are each an integer of 1 to 4,
r2 and r3 are each an integer of 1 to 3,
When r1 is 2 or more, the two or more R1 are the same as or different from each other,
When r2 is 2 or more, the two or more R2 are the same as or different from each other,
When r3 is 2 or more, the two or more R3 are the same as or different from each other,
When r4 is 2 or more, the two or more R4s are the same as or different from each other,
When r6 is 2 or more, the two or more R6 are the same as or different from each other,
When r7 is 2 or more, the two or more R7s are the same as or different from each other,
When Ar1 is hydrogen,

Wow

Are different from each other,

Means a site bonded to the formula (1). The compound of claim 1, wherein Formula 1 is represented by Formula 1-1 or 1-2:
[Formula 1-1]

[Formula 1-2]

In Chemical Formulas 1-1 and 1-2,
Ar11 is a straight or branched chain alkyl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms,
Definitions of R1 to R7, r1 to r4, r6 and r7 are the same as defined in the formula (1). The compound of claim 1, wherein R5 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms. The method according to claim 1, wherein R1, R6 and R7 are the same as or different from each other, each independently hydrogen; Linear or branched alkyl groups having 1 to 30 carbon atoms; Monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms; Or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or adjacent groups are bonded to each other to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms Compound. The method according to claim 1, wherein Ar1 is hydrogen; Linear or branched alkyl groups having 1 to 30 carbon atoms; Or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms. The compound of claim 1, wherein Formula 1 is selected from the following compounds:

. A first electrode; A second electrode provided to face the first electrode; And at least one organic material layer including a light emitting layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound of any one of claims 1 to 6. Organic light emitting device. The organic light emitting device of claim 7, wherein the light emitting layer comprises the compound. The organic light emitting device of claim 7, wherein the light emitting layer comprises the compound as a dopant of the light emitting layer. The organic light emitting diode of claim 9, wherein a maximum emission wavelength of the dopant is 450 nm to 650 nm. The organic light emitting device of claim 7, wherein the light emitting layer comprises a host. The organic light emitting device of claim 7, wherein the light emitting layer comprises the compound as a dopant of the light emitting layer, and includes at least one selected from Formulas A to F as a host of the light emitting layer.
[Formula A]

In Chemical Formula A,
Y11 is NR ', S or O,
q1 is an integer of 0 to 3,
R 'is a straight or branched chain alkyl group having 1 to 30 carbon atoms; Or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms,
[Formula B]

In Chemical Formula B,
Y12 is O or S,
L1 is a biphenylylene group; A fluorenylene group unsubstituted or substituted with a linear or branched alkyl group having 1 to 30 carbon atoms or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a spirobifluorenylene group,
A1 is a carbazolyl unsubstituted or substituted with a silyl group substituted with a straight or branched chain alkyl group having 1 to 30 carbon atoms, a straight or branched chain alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms. Qi
[Formula C]

In Chemical Formula C,
Q1 to Q8 are the same as or different from each other, and each independently hydrogen; Monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with a heteroaryl group having 2 to 30 carbon atoms; Or a heteroaryl group having 2 to 30 carbon atoms, or adjacent groups are bonded to each other to form a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a monocyclic group having 2 to 30 carbon atoms unsubstituted or substituted with a heteroaryl group having 2 to 30 carbon atoms. To form a heterocycle of the ring,
[Formula D]

[Formula E]

In Chemical Formulas D and E,
Y13 and Y14 are the same as or different from each other, and each independently O or S,
Z1 to Z6 are the same as or different from each other, and each independently N or CR ",
L2 and L3 are the same as or different from each other, and each independently a direct bond; Monocyclic or polycyclic arylene groups having 6 to 30 carbon atoms; Or a monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms,
A2 and A3 are the same as or different from each other, and each independently cyano group; Substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms,
R ″ and G1 to G4 are the same as or different from each other, and each independently hydrogen; deuterium; cyano group; halogen group; substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; substituted or unsubstituted carbon atom 6 Or a monocyclic or polycyclic aryl group of 30 to 30, or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, or adjacent groups combine with each other to form a substituted or unsubstituted ring,
g1 and g3 are each an integer of 1 to 7,
g2 is an integer of 1 to 3,
g4 is an integer of 1 to 8,
When g1 is 2 or more, the two or more G1 are the same as or different from each other,
When g2 is 2 or more, the two or more G2s are the same as or different from each other,
When g3 is 2 or more, the two or more G3 are the same as or different from each other,
When g4 is 2 or more, the two or more G4 are the same as or different from each other,
Formula F]

In Chemical Formula F,
L13 is a substituted or unsubstituted (b + 1) valent aryl group; Or a (b + 1) valent heteroaryl group,
G11 and G12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Cyano group; Or a heteroaryl group containing O or S,
b13 is an integer of 1 to 3, when b13 is 2 or more, L13 is the same as or different from each other,
b is 1 or 2, if b is 2

Are the same as or different from each other. The organic light emitting device of claim 12, wherein the light emitting layer comprises the dopant and the host in a weight ratio of 1:99 to 50:50.

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