KR102616387B1 - Organic light emitting device - Google Patents

Abstract

This specification includes: a first electrode; second electrode; a light emitting layer provided between the first electrode and the second electrode; and a first organic layer provided between the first electrode and the light-emitting layer, wherein the first organic layer includes a compound represented by Formula 1, and the light-emitting layer includes a compound represented by Formula 2. Devices are provided.

Description

Organic light emitting device {ORGANIC LIGHT EMITTING DEVICE}

This application claims the benefit of the filing date of Korean Patent Application No. 10-2019-0086858 filed with the Korea Intellectual Property Office on July 18, 2019, the entire contents of which are incorporated herein by reference.

This specification relates to organic light emitting devices.

Organic light emitting devices have a structure in which an organic thin film is placed between two electrodes. When voltage is applied to an organic light-emitting device with this structure, electrons and holes injected from two electrodes combine in the organic thin film to form a pair and then annihilate, emitting light. The organic thin film may be composed of a single layer or multiple layers as needed.

Most of the materials used in organic light-emitting devices are pure organic materials or complexes of organic materials and metals. Depending on the application, hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, etc. It can be divided into: Here, organic materials with p-type properties, that is, organic materials that are easily oxidized and have an electrochemically stable state upon oxidation, are mainly used as hole injection materials or hole transport materials. Meanwhile, organic materials with n-type properties, that is, organic materials that are easily reduced and have an electrochemically stable state upon reduction, are mainly used as electron injection materials or electron transport materials. The emitting layer material is preferably a material that has both p-type and n-type properties, that is, a material that is stable in both oxidation and reduction states, and excitons are formed when holes and electrons recombine in the emitting layer. A material with high luminous efficiency that converts light into light is desirable.

In order to improve the performance, lifespan, or efficiency of organic light-emitting devices, the development of organic thin film materials is continuously required.

Korean Patent Publication No. 10-2017-058618

An organic light emitting device having low driving voltage, high efficiency, and long lifespan characteristics is described herein.

One embodiment of this specification is

first electrode;

second electrode;

a light emitting layer provided between the first electrode and the second electrode; and

In the organic light-emitting device comprising a first organic material layer provided between the first electrode and the light-emitting layer,

The first organic layer includes a compound represented by the following formula (1),

The light emitting layer provides an organic light emitting device including a compound represented by the following formula (2).

[Formula 1]

In Formula 1,

Ar1 is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

L1 to L3 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted alkylene group; Substituted or unsubstituted arylene group; A substituted or unsubstituted divalent alkoxy group; A substituted or unsubstituted divalent alkenyl group; Or a substituted or unsubstituted divalent heterocyclic group,

R1 to R6 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Nitrile group; Substituted or unsubstituted silyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

r1 to r4 are the same or different from each other and are each independently an integer of 0 to 4,

When r1 to r4 are integers of 2 or more, the substituents in parentheses are the same or different from each other,

[Formula 2]

In Formula 2,

R7 to R11 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Nitrile group; Substituted or unsubstituted amine group; Substituted or unsubstituted silyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

r7 is an integer from 1 to 3,

r8 and r9 are the same or different from each other and are each independently an integer of 1 to 5,

r10 and r11 are the same or different from each other and are each independently an integer of 1 to 4,

When r7 to r11 are integers of 2 or more, the substituents in parentheses are the same or different from each other.

The organic light-emitting device of the present invention includes a compound represented by Formula 1 in the first organic material layer and a compound represented by Formula 2 in the light-emitting layer, thereby obtaining an organic light-emitting device having low driving voltage, high efficiency, and/or long lifespan. You can.

Figure 1 shows an example of an organic light emitting device consisting of a substrate 1, an anode 2, a light emitting layer 6, and a cathode 10.
Figure 2 shows an example of an organic light emitting device consisting of a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a light emitting layer 6, an electron transport layer 8, and a cathode 10. It was done.
3 shows a substrate (1), an anode (2), a hole injection layer (3), a hole transport layer (4), an electron blocking layer (5), a light emitting layer (6), a hole blocking layer (7), and an electron transport layer (8). , an electron injection layer (9), and a cathode (10).

Hereinafter, this specification will be described in more detail.

The organic light emitting device of the present invention is

first electrode;

second electrode;

a light emitting layer provided between the first electrode and the second electrode; and

In the organic light-emitting device comprising a first organic material layer provided between the first electrode and the light-emitting layer,

The first organic layer includes a compound represented by the following formula (1),

The light-emitting layer includes a compound represented by the following formula (2).

[Formula 1]

In Formula 1,

Ar1 is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

L1 to L3 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted alkylene group; Substituted or unsubstituted arylene group; A substituted or unsubstituted divalent alkoxy group; A substituted or unsubstituted divalent alkenyl group; Or a substituted or unsubstituted divalent heterocyclic group,

R1 to R6 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Nitrile group; Substituted or unsubstituted silyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

r1 to r4 are the same or different from each other and are each independently an integer of 0 to 4,

When r1 to r4 are integers of 2 or more, the substituents in parentheses are the same or different from each other,

[Formula 2]

In Formula 2,

R7 to R11 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Nitrile group; Substituted or unsubstituted amine group; Substituted or unsubstituted silyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

r7 is an integer from 1 to 3,

r8 and r9 are the same or different from each other and are each independently an integer of 1 to 5,

r10 and r11 are the same or different from each other and are each independently an integer of 1 to 4,

When r7 to r11 are integers of 2 or more, the substituents in parentheses are the same or different from each other.

In this specification, when a part “includes” a certain component, this means that it may further include other components rather than excluding other components, unless specifically stated to the contrary.

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

In this specification, " "refers to a chemical formula or a position bonded to a compound.

Examples of substituents in this specification are described below, but are not limited thereto.

The term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent. The position to be substituted is not limited as long as it is the position where the hydrogen atom is substituted, that is, a position where the substituent can be substituted, and if two or more substituents are substituted. , two or more substituents may be the same or different from each other.

As used herein, the term “substituted or unsubstituted” refers to deuterium; halogen group; Nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imide group; amino group; silyl group; boron group; Alkoxy group; Aryloxy group; Alkyl group; Cycloalkyl group; Aryl group; and a heterocyclic group, or is substituted with a substituent in which two or more of the above-exemplified substituents are linked, or does not have any substituent. For example, “a substituent group in which two or more substituents are connected” may be a biphenyl group. That is, the biphenyl group may be an aryl group, or it may be interpreted as a substituent in which two phenyl groups are connected.

As used herein, the term “substituted or unsubstituted” refers to deuterium; halogen group; Amine group; silyl group; Alkyl group; Cycloalkyl group; Aryl group; and a heterocyclic group, or is substituted with a substituent in which two or more of the above-exemplified substituents are linked, or does not have any substituent.

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

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

In this specification, the carbon number of the carbonyl group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, it may be a compound with the following structure, but is not limited thereto.

In the present specification, the oxygen of the ester group may be substituted with a straight-chain, branched-chain, or ring-chain alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In this specification, the carbon number of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound with the following structure, but is not limited thereto.

In the present specification, the silyl group may be represented by the formula -SiY _a Y _b Y _c , where Y _a , Y _b and Y _c are each hydrogen; Substituted or unsubstituted alkyl group; Or, it may be a substituted or unsubstituted aryl group. The silyl group specifically includes, but is not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, and phenylsilyl group. No.

In the present specification, the boron group may be represented by the chemical formula -BY _{dY e} , where Y _d and Y _e are each hydrogen; Substituted or unsubstituted alkyl group; Or, it may be a substituted or unsubstituted aryl group. The boron group specifically includes, but is not limited to, trimethyl boron group, triethyl boron group, t-butyldimethyl boron group, triphenyl boron group, and phenyl boron group.

In the present specification, the alkyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the carbon number of the alkyl group is 1 to 30. According to another embodiment, the carbon number of the alkyl group is 1 to 20. According to another embodiment, the carbon number of the alkyl group is 1 to 10. Specific examples of alkyl groups 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, etc., but are not limited to these.

In the present specification, the alkoxy group may be straight chain, branched chain, or ring chain. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n. -Hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, etc., but is not limited thereto.

Substituents containing alkyl groups, alkoxy groups, and other alkyl group moieties described in this specification include both straight-chain or branched forms.

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 embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 6. Specifically, it includes cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, etc., 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 one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group, such as a phenyl group, biphenyl group, terphenyl group, or quarterphenyl group, but is not limited thereto. The polycyclic aryl group may include a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenyl group, chrysenyl group, fluorenyl group, triphenylenyl group, etc., but is not limited thereto. no.

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

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-diphenylfluorenyl group). However, it is not limited to this.

In the present specification, the above-described description of the aryl group may be applied to the aryl group in the aryloxy group.

In the present specification, the heterocyclic group is a cyclic group containing one or more of N, O, P, S, Si, and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but it is preferably 2 to 60 carbon atoms. According to one embodiment, the carbon number of the heterocyclic group is 2 to 30. Examples of heterocyclic groups include pyridine group, pyrrole group, pyrimidine group, quinoline group, pyridazinyl group, furan group, thiophene group, imidazole group, pyrazole group, dibenzofuran group, and dibenzothiophene group. , carbazole group, benzocarbazole group, naphthobenzofuran group, benzonaphthothiophene group, indenocarbazole group, etc., but is not limited to these.

In the present specification, the description regarding the heterocyclic group described above may be applied, except that the heteroaryl group is aromatic.

In the present specification, in a substituted or unsubstituted ring formed by combining adjacent groups, “ring” refers to a hydrocarbon ring; Or it means a heterocycle.

The hydrocarbon ring may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and may be selected from examples of the cycloalkyl group or aryl group.

In the present specification, the above description of the aryl group may be applied to the aromatic hydrocarbon ring.

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

In the present specification, the above description of the heteroaryl group can be applied, except that the heteroarylene group is divalent.

In the present specification, the description of the heterocyclic group can be applied, except that the divalent heterocyclic ring is divalent.

Hereinafter, Chemical Formula 1 will be described in detail.

[Formula 1]

In Formula 1,

Ar1 is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

L1 to L3 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted alkylene group; Substituted or unsubstituted arylene group; A substituted or unsubstituted divalent alkoxy group; A substituted or unsubstituted divalent alkenyl group; Or a substituted or unsubstituted divalent heterocyclic group,

R1 to R6 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Nitrile group; Substituted or unsubstituted silyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

r1 to r4 are the same or different from each other and are each independently an integer of 0 to 4,

When r1 to r4 are integers of 2 or more, the substituents in parentheses are the same as or different from each other.

According to an exemplary embodiment of the present specification, Ar1 is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heterocyclic group.

According to an exemplary embodiment of the present specification, Ar1 is hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heterocyclic group.

According to an exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heterocyclic group.

According to an exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or it is a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

According to an exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or it is a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted aryl group having 6 to 15 carbon atoms; Or it is a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms.

According to an exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; Or it is a substituted or unsubstituted heterocyclic group having 2 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted phenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted triphenylenyl group; Substituted or unsubstituted fluorenyl group; A substituted or unsubstituted spirobifluorenyl group; Substituted or unsubstituted carbazole group; Substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.

According to an exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted phenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted triphenylenyl group; Substituted or unsubstituted fluorenyl group; Or a substituted or unsubstituted spirobifluorenyl group.

According to an exemplary embodiment of the present specification, Ar1 is a phenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, an alkyl group, and an aryl group; A naphthyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, alkyl group, and aryl group; A biphenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, alkyl group, and aryl group; A terphenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, alkyl group, and aryl group; A phenanthrenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, alkyl group, and aryl group; A triphenylenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, alkyl group, and aryl group; A fluorenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, alkyl group, and aryl group; Or it is a spirobifluorenyl group substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, alkyl group, and aryl group.

According to an exemplary embodiment of the present specification, Ar1 is a phenyl group unsubstituted or substituted with deuterium; Naphthyl group substituted or unsubstituted with deuterium; Biphenyl group substituted or unsubstituted with deuterium; Terphenyl group substituted or unsubstituted with deuterium; A phenanthrenyl group substituted or unsubstituted with deuterium; Triphenylenyl group substituted or unsubstituted with deuterium; A fluorenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, methyl group, and phenyl group; Or it is a spirobifluorenyl group substituted or unsubstituted with deuterium.

According to an exemplary embodiment of the present specification, Ar1 is a phenyl group unsubstituted or substituted with deuterium; naphthyl group; Biphenyl group substituted or unsubstituted with deuterium; Terphenyl group; phenanthrenyl group; Triphenylenyl group; dimethylfluorenyl group; Diphenyl fluorenyl group; Or it is a spirobifluorenyl group.

In one embodiment of the present specification, Ar1 is represented by one of the following formulas.

In the above formula, R is hydrogen; heavy hydrogen; halogen group; Nitrile group; Substituted or unsubstituted silyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

The dotted line indicates the binding site where L1 is bound.

According to an exemplary embodiment of the present specification, R is a substituted or unsubstituted alkyl group; Or it is a substituted or unsubstituted aryl group.

According to an exemplary embodiment of the present specification, R is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or it is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, R is an alkyl group having 1 to 30 carbon atoms; Or it is an aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, R is a methyl group; Or it is a phenyl group.

In one embodiment of the present specification, Ar1 is represented by one of the following formulas.

In the above formula, the definition of R is as described above, and the dotted line indicates the binding site where it is bonded to L1.

According to an exemplary embodiment of the present specification, Ar1 is a phenyl group; Or it is a biphenyl group.

According to an exemplary embodiment of the present specification, Ar1 may be substituted with deuterium.

According to an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently directly bonded; Substituted or unsubstituted alkylene group; Substituted or unsubstituted arylene group; A substituted or unsubstituted divalent alkoxy group; A substituted or unsubstituted divalent alkenyl group; Or it is a substituted or unsubstituted divalent heterocyclic group.

According to an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently directly bonded; Substituted or unsubstituted arylene group; Or it is a substituted or unsubstituted divalent heterocyclic group.

According to an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently directly bonded; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted divalent heterocyclic group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently directly bonded; A substituted or unsubstituted arylene group having 6 to 20 carbon atoms; Or it is a substituted or unsubstituted divalent heterocyclic group having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently directly bonded; A substituted or unsubstituted arylene group having 6 to 15 carbon atoms; Or it is a substituted or unsubstituted divalent heterocyclic group having 2 to 15 carbon atoms.

According to an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently directly bonded; A substituted or unsubstituted arylene group having 6 to 10 carbon atoms; Or it is a substituted or unsubstituted divalent heterocyclic group having 2 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently directly bonded; Or it is a substituted or unsubstituted arylene group.

According to an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently directly bonded; Or it is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently directly bonded; Or it is a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently directly bonded; Substituted or unsubstituted phenylene group; Substituted or unsubstituted naphthylene group; Substituted or unsubstituted biphenylene group; Substituted or unsubstituted terphenylene group; Substituted or unsubstituted phenanthrenylene group; Substituted or unsubstituted triphenylenylene group; Or it is a substituted or unsubstituted fluorenylene group.

According to an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently directly bonded; A phenylene group substituted or unsubstituted by deuterium, an alkyl group, or an aryl group; A naphthylene group substituted or unsubstituted with deuterium, an alkyl group, or an aryl group; A biphenylene group substituted or unsubstituted with deuterium, an alkyl group, or an aryl group; A terphenylene group substituted or unsubstituted with deuterium, an alkyl group, or an aryl group; A phenanthrenylene group substituted or unsubstituted with deuterium, an alkyl group, or an aryl group; A triphenylenenylene group substituted or unsubstituted with deuterium, an alkyl group, or an aryl group; Or it is a fluorenylene group substituted or unsubstituted with deuterium, an alkyl group, or an aryl group.

According to an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently directly bonded; A phenylene group substituted or unsubstituted by deuterium, an alkyl group, or an aryl group; A naphthylene group substituted or unsubstituted with deuterium, an alkyl group, or an aryl group; A biphenylene group substituted or unsubstituted with deuterium, an alkyl group, or an aryl group; Or it is a fluorenylene group substituted or unsubstituted with deuterium, an alkyl group, or an aryl group.

According to an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently directly bonded; A phenylene group substituted or unsubstituted with deuterium; naphthylene group; Biphenylene group; Or it is a dimethylfluorenylene group.

According to an exemplary embodiment of the present specification, L1 are the same or different from each other, and are each independently directly bonded; Substituted or unsubstituted phenylene group; Substituted or unsubstituted naphthylene group; Substituted or unsubstituted biphenylene group; Substituted or unsubstituted terphenylene group; Substituted or unsubstituted phenanthrenylene group; Substituted or unsubstituted triphenylenylene group; Or it is a substituted or unsubstituted fluorenylene group.

According to an exemplary embodiment of the present specification, L1 are the same or different from each other, and are each independently directly bonded; A phenylene group substituted or unsubstituted by deuterium, an alkyl group, or an aryl group; A naphthylene group substituted or unsubstituted with deuterium, an alkyl group, or an aryl group; A biphenylene group substituted or unsubstituted with deuterium, an alkyl group, or an aryl group; A terphenylene group substituted or unsubstituted with deuterium, an alkyl group, or an aryl group; A phenanthrenylene group substituted or unsubstituted with deuterium, an alkyl group, or an aryl group; A triphenylenenylene group substituted or unsubstituted with deuterium, an alkyl group, or an aryl group; Or it is a fluorenylene group substituted or unsubstituted with deuterium, an alkyl group, or an aryl group.

According to an exemplary embodiment of the present specification, L1 are the same or different from each other, and are each independently directly bonded; A phenylene group substituted or unsubstituted by deuterium, an alkyl group, or an aryl group; A naphthylene group substituted or unsubstituted with deuterium, an alkyl group, or an aryl group; A biphenylene group substituted or unsubstituted with deuterium, an alkyl group, or an aryl group; Or it is a fluorenylene group substituted or unsubstituted with deuterium, an alkyl group, or an aryl group.

According to an exemplary embodiment of the present specification, L1 are the same or different from each other, and are each independently directly bonded; A phenylene group substituted or unsubstituted with deuterium; naphthylene group; Biphenylene group; It is a dimethylfluorenylene group.

According to an exemplary embodiment of the present specification, L2 is a direct bond; Substituted or unsubstituted phenylene group; Or a substituted or unsubstituted biphenylene group.

According to an exemplary embodiment of the present specification, L2 is a phenylene group substituted or unsubstituted with deuterium or an aryl group; Or it is a biphenylene group substituted or unsubstituted with deuterium or aryl group.

According to an exemplary embodiment of the present specification, L3 is a direct bond; Substituted or unsubstituted phenylene group; Or a substituted or unsubstituted biphenylene group.

According to an exemplary embodiment of the present specification, L3 is a phenylene group substituted or unsubstituted with deuterium or an aryl group; Or it is a biphenylene group substituted or unsubstituted with deuterium or aryl group.

According to an exemplary embodiment of the present specification, L2 and L3 are the same as or different from each other, and are each independently directly bonded; A phenylene group substituted or unsubstituted with deuterium; Or it is a biphenylene group substituted or unsubstituted with deuterium.

According to an exemplary embodiment of the present specification, L2 and L3 are the same as or different from each other, and are each independently directly bonded; A phenylene group substituted or unsubstituted with deuterium; Or it is a biphenylene group.

According to an exemplary embodiment of the present specification, L1 to L3 are direct bonds or are represented by one of the following formulas.

In the above formula,

R' and R'' are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Nitrile group; Substituted or unsubstituted silyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

The dotted line indicates the binding position.

According to an exemplary embodiment of the present specification, R' and R'' are the same or different from each other, and are each independently a substituted or unsubstituted alkyl group; Or it is a substituted or unsubstituted aryl group.

According to an exemplary embodiment of the present specification, R' and R'' are the same or different from each other, and are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or it is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, R' and R'' are the same or different from each other, and are each independently an alkyl group having 1 to 30 carbon atoms; Or it is an aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, R' and R'' are the same or different from each other, and are each independently a methyl group; Or it is a phenyl group.

According to an exemplary embodiment of the present specification, L1 to L3 are direct bonds or are represented by one of the following formulas.

In the above formula, the dotted line indicates the bonding position.

According to an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently directly bonded; phenylene group; Or it is a biphenylene group.

According to an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and are each independently a phenylene group; Or it is a biphenylene group.

According to an exemplary embodiment of the present specification, L1 to L3 may each be replaced with deuterium.

According to an exemplary embodiment of the present specification, R1 to R6 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Nitrile group; Substituted or unsubstituted silyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heterocyclic group.

According to an exemplary embodiment of the present specification, R1 to R6 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Or it is a substituted or unsubstituted aryl group.

According to an exemplary embodiment of the present specification, R1 to R6 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Or it is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

According to an exemplary embodiment of the present specification, R1 to R6 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Or it is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, R1 to R6 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Or it is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, R1 to R6 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted phenyl group.

According to an exemplary embodiment of the present specification, R1 to R6 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Or it is a phenyl group.

According to an exemplary embodiment of the present specification, R1 to R4 are hydrogen.

According to an exemplary embodiment of the present specification, R5 and R6 are the same as or different from each other, and are each independently hydrogen; Or it is a phenyl group.

According to an exemplary embodiment of the present specification, R1 to R6 are hydrogen.

According to an exemplary embodiment of the present specification, r1 to r4 are the same or different from each other and are each independently an integer of 0 to 4, and when r1 to r4 are integers of 2 or more, the substituents in parentheses are the same or different from each other.

According to an exemplary embodiment of the present specification, r1 to r4 are each integers from 1 to 4.

According to an exemplary embodiment of the present specification, r1 to r4 are 1.

According to an exemplary embodiment of the present specification, r1 to r4 are 4.

According to an exemplary embodiment of the present specification, the compound represented by Formula 1 has a left-right symmetrical structure with respect to the Z1 axis as shown in the following structural formula.

According to an exemplary embodiment of the present specification, the compound represented by Formula 1 has a left-right asymmetric structure with respect to the Z1 axis as shown in the following structural formula.

Hereinafter, Formula 2 will be described in detail.

[Formula 2]

In Formula 2,

R7 to R11 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Nitrile group; Substituted or unsubstituted amine group; Substituted or unsubstituted silyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

r7 is an integer from 1 to 3,

r8 and r9 are the same or different from each other and are each independently an integer of 1 to 5,

r10 and r11 are the same or different from each other and are each independently an integer of 1 to 4,

When r7 to r11 are integers of 2 or more, the substituents in parentheses are the same or different from each other.

According to an exemplary embodiment of the present specification, R7 to R11 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Nitrile group; Substituted or unsubstituted amine group; Substituted or unsubstituted silyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heterocyclic group.

According to an exemplary embodiment of the present specification, R7 to R11 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted amine group; Substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, R7 to R11 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted amine group; Substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or it is a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, R7 to R11 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Substituted or unsubstituted amine group; Substituted or unsubstituted silyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted pyridyl group; Substituted or unsubstituted carbazole group; Or a substituted or unsubstituted hexahydrocarbazole group.

According to an exemplary embodiment of the present specification, R7 is hydrogen; heavy hydrogen; Substituted or unsubstituted amine group; Substituted or unsubstituted silyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heterocyclic group.

According to an exemplary embodiment of the present specification, R7 is hydrogen; heavy hydrogen; An amine group substituted or unsubstituted with one or more substituents or two or more substituents selected from the group consisting of an alkyl group, a halogen group, a cycloalkyl group, and an aryl group; A silyl group substituted or unsubstituted with one or more substituents or two or more substituents selected from the group consisting of an alkyl group, a halogen group, a cycloalkyl group, and an aryl group; an alkyl group substituted or unsubstituted with one or more substituents or two or more substituents selected from the group consisting of an alkyl group, a halogen group, a cycloalkyl group, and an aryl group; A substituted or unsubstituted aryl group consisting of one or more substituents or two or more substituents selected from the group consisting of an alkyl group, a halogen group, a cycloalkyl group, and an aryl group; Or, it is a substituted or unsubstituted heterocyclic group consisting of one or more substituents or two or more substituents selected from the group consisting of an alkyl group, halogen group, cycloalkyl group, and aryl group.

According to an exemplary embodiment of the present specification, R7 is hydrogen; heavy hydrogen; An amine group substituted or unsubstituted with one or more substituents or two or more substituents selected from the group consisting of an alkyl group, a halogen group, a cycloalkyl group, and an aryl group; A silyl group substituted or unsubstituted with one or more substituents or two or more substituents selected from the group consisting of an alkyl group, a halogen group, a cycloalkyl group, and an aryl group; an alkyl group substituted or unsubstituted with one or more substituents or two or more substituents selected from the group consisting of an alkyl group, a halogen group, a cycloalkyl group, and an aryl group; A substituted or unsubstituted aryl group consisting of one or more substituents or two or more substituents selected from the group consisting of an alkyl group, a halogen group, a cycloalkyl group, and an aryl group; A carbazole group substituted or unsubstituted with one or more substituents or two or more substituents selected from the group consisting of an alkyl group, a halogen group, a cycloalkyl group, and an aryl group; Or, it is a substituted or unsubstituted hexahydrocarbazole group in which one or more substituents or two or more substituents selected from the group consisting of an alkyl group, halogen group, cycloalkyl group, and aryl group are connected.

According to an exemplary embodiment of the present specification, R7 is hydrogen; heavy hydrogen; an alkyl group having 1 to 10 carbon atoms; An amine group substituted or unsubstituted with one or more substituents or two or more substituents selected from the group consisting of an alkyl group with 1 to 10 carbon atoms, a halogen group, a cycloalkyl group with 3 to 10 carbon atoms, and an aryl group with 6 to 20 carbon atoms; A silyl group substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, wherein one or more substituents or two or more substituents selected from the group consisting of alkyl groups and silyl groups having 1 to 10 carbon atoms are linked; Or it is a heterocyclic group substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, R7 is hydrogen; heavy hydrogen; methyl group; t-butyl group; trimethylsilyl group; An amine group unsubstituted or substituted with one or more substituents selected from the group consisting of methyl group, t-butyl group, fluorine group, cyclohexyl group, and phenyl group; A phenyl group substituted or unsubstituted with trimethylsilyl group; Carbazole group substituted or unsubstituted with a methyl group or t-butyl group; Or it is a hexahydrocarbazole group substituted or unsubstituted with a methyl group.

According to an exemplary embodiment of the present specification, R7 is hydrogen; methyl group; t-butyl group; trimethylsilyl group; An amine group unsubstituted or substituted with one or more substituents selected from the group consisting of methyl group, t-butyl group, fluorine group, cyclohexyl group, and phenyl group; A phenyl group substituted or unsubstituted with trimethylsilyl group; Carbazole group substituted or unsubstituted with a methyl group or t-butyl group; Or it is a hexahydrocarbazole group substituted or unsubstituted with a methyl group.

According to an exemplary embodiment of the present specification, R7 is hydrogen; methyl group; t-butyl group; trimethylsilyl group; An amine group substituted or unsubstituted with a phenyl group substituted or unsubstituted with a methyl group, t-butyl group, or fluorine group; An amine group substituted or unsubstituted with a cyclohexyl group; A phenyl group substituted or unsubstituted with trimethylsilyl group; Carbazole group substituted or unsubstituted with t-butyl group; Or it is a hexahydrocarbazole group substituted or unsubstituted with a methyl group.

According to an exemplary embodiment of the present specification, R7 is represented by one of the following structural formulas.

In the above structural formula means the binding position.

According to an exemplary embodiment of the present specification, R7 is represented by one of the following structural formulas.

In the above structural formula means the binding position.

According to an exemplary embodiment of the present specification, R7 is hydrogen; Or it is an amine group substituted or unsubstituted with a phenyl group substituted or unsubstituted with a t-butyl group.

According to an exemplary embodiment of the present specification, R8 and R9 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heterocyclic group.

According to an exemplary embodiment of the present specification, R8 and R9 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Substituted or unsubstituted amine group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, R8 and R9 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Substituted or unsubstituted amine group; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or it is a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, R8 and R9 are the same as or different from each other, and are each independently hydrogen; An amine group substituted or unsubstituted with one or more substituents or two or more substituents selected from the group consisting of deuterium, alkyl group, halogen group, silyl group, cycloalkyl group, and aryl group; A silyl group substituted or unsubstituted with one or more substituents or two or more substituents selected from the group consisting of deuterium, alkyl group, halogen group, silyl group, cycloalkyl group, and aryl group; an alkyl group substituted or unsubstituted with one or more substituents or two or more substituents selected from the group consisting of deuterium, alkyl group, halogen group, silyl group, cycloalkyl group, and aryl group; A carbazole group substituted or unsubstituted with one or more substituents or two or more substituents selected from the group consisting of deuterium, alkyl group, halogen group, silyl group, cycloalkyl group, and aryl group; Or, it is a pyridyl group substituted or unsubstituted with one or more substituents or two or more substituents selected from the group consisting of deuterium, alkyl group, halogen group, silyl group, cycloalkyl group, and aryl group connected.

According to an exemplary embodiment of the present specification, R8 and R9 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group with one or more substituents or two or more substituents selected from the group consisting of deuterium, an alkyl group, a halogen group, a silyl group, and an aryl group, and a substituted or unsubstituted alkyl group; An amine group substituted or unsubstituted with one or more substituents or two or more substituents selected from the group consisting of deuterium, alkyl group, halogen group, silyl group, and aryl group; A substituted or unsubstituted aryl group with one or more substituents or two or more substituents selected from the group consisting of deuterium, alkyl group, halogen group, silyl group, and aryl group; Or, it is a substituted or unsubstituted heterocyclic group consisting of one or more substituents or two or more substituents selected from the group consisting of deuterium, alkyl group, halogen group, silyl group, and aryl group.

According to an exemplary embodiment of the present specification, R8 and R9 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; an alkyl group having 1 to 10 carbon atoms; An amine group substituted or unsubstituted with one or more substituents or two or more substituents selected from the group consisting of an alkyl group having 1 to 10 carbon atoms and an aryl group having 6 to 20 carbon atoms; an aryl group having 6 to 20 carbon atoms, substituted or unsubstituted with one or more substituents or two or more substituents selected from the group consisting of deuterium, an alkyl group with 1 to 10 carbon atoms, a halogen group, and a silyl group; Or, it is a heterocyclic group having 2 to 20 carbon atoms that is substituted or unsubstituted with one or more substituents or two or more substituents selected from the group consisting of deuterium, an alkyl group with 1 to 10 carbon atoms, and an aryl group with 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, R8 and R9 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; methyl group; t-butyl group; An amine group substituted or unsubstituted with a phenyl group; A phenyl group substituted or unsubstituted with one or more substituents or two or more substituents selected from the group consisting of deuterium, methyl group, t-butyl group, fluorine group, and silyl group; Or, it is a pyridyl group substituted or unsubstituted by one or more substituents or two or more substituents selected from the group consisting of deuterium, methyl group, t-butyl group, or phenyl group.

According to an exemplary embodiment of the present specification, R8 and R9 are the same as or different from each other, and are each independently hydrogen; methyl group; t-butyl group; Diphenylamine group; A phenyl group unsubstituted or substituted with deuterium, methyl group, t-butyl group, fluorine group, CF ₃ or trimethylsilyl group; Or it is a pyridyl group substituted or unsubstituted with a methyl group, t-butyl group, CD ₃ or phenyl group.

According to an exemplary embodiment of the present specification, R8 and R9 are the same as or different from each other, and may each independently be represented by one of the following structural formulas.

In the above structural formula means the binding position.

According to an exemplary embodiment of the present specification, R8 and R9 are the same as or different from each other, and may each independently be represented by one of the following structural formulas.

In the above structural formula means the binding position.

According to an exemplary embodiment of the present specification, R8 and R9 are the same as or different from each other, and are each independently hydrogen; Or it is a t-butyl group.

According to an exemplary embodiment of the present specification, R10 and R11 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted silyl group; Substituted or unsubstituted amine group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heterocyclic group.

According to an exemplary embodiment of the present specification, R10 and R11 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A silyl group substituted or unsubstituted by an alkyl group or an aryl group; An amine group unsubstituted or substituted by an alkyl group, an arylalkyl group, or an aryl group; An alkyl group substituted or unsubstituted by an alkyl group or an aryl group; Aryl group substituted or unsubstituted by an alkyl group or an aryl group; Or it is a heterocyclic group substituted or unsubstituted by an alkyl group or an aryl group.

According to an exemplary embodiment of the present specification, R10 and R11 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A silyl group substituted or unsubstituted by an alkyl group or an aryl group; An amine group substituted or unsubstituted by an alkyl group or an aryl group; An alkyl group substituted or unsubstituted by an alkyl group or an aryl group; Aryl group substituted or unsubstituted by an alkyl group or an aryl group; Or it is a heterocyclic group substituted or unsubstituted by an alkyl group or an aryl group.

According to an exemplary embodiment of the present specification, R10 and R11 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A silyl group substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms; An amine group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, an arylalkyl group having 6 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms; an alkyl group having 1 to 10 carbon atoms; Aryl group having 6 to 20 carbon atoms; Or it is a heterocyclic group having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, R10 and R11 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A silyl group substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms; An amine group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 20 carbon atoms; an alkyl group having 1 to 10 carbon atoms; Aryl group having 6 to 20 carbon atoms; Or it is a heterocyclic group having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, R10 and R11 are the same as or different from each other, and are each independently hydrogen; methyl group; t-butyl group; trimethylsilyl group; phenyl group; carbazole group; Or, it is an amine group substituted with a phenyl group.

According to an exemplary embodiment of the present specification, R10 and R11 are the same as or different from each other, and are each independently hydrogen; methyl group; t-butyl group; trimethylsilyl group; phenyl group; carbazole group; Or it is a diphenylamine group.

According to an exemplary embodiment of the present specification, if one of R10 and R11 is a substituted or unsubstituted carbazole group or a substituted or unsubstituted amine group, the other is hydrogen.

According to an exemplary embodiment of the present specification, R10 and R11 are the same as or different from each other, and may each independently be represented by one of the following structural formulas.

In the above structural formula means the binding position.

According to an exemplary embodiment of the present specification, R10 and R11 are the same as or different from each other, and may each independently be represented by one of the following structural formulas.

In the above structural formula means the binding position.

According to an exemplary embodiment of the present specification, R10 and R11 are hydrogen; Or it is a t-butyl group.

According to an exemplary embodiment of the present specification, r7 is an integer from 1 to 3.

According to an exemplary embodiment of the present specification, r7 is 1.

According to an exemplary embodiment of the present specification, r8 and r9 are integers from 1 to 5.

According to an exemplary embodiment of the present specification, r8 and r9 are integers from 1 to 3.

According to an exemplary embodiment of the present specification, r10 and r11 are integers from 1 to 4.

According to an exemplary embodiment of the present specification, r10 and r11 are 1.

According to an exemplary embodiment of the present specification, when r7 to r11 are an integer of 2 or more, the substituents in parentheses are the same or different from each other.

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

[Formula 2-1]

[Formula 2-2]

In Formulas 2-1 and 2-2,

The definitions of R8 to R11 and r7 to r11 are the same as those in Formula 2 described above,

R7' is hydrogen; heavy hydrogen; halogen group; Nitrile group; Substituted or unsubstituted silyl group; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

G1 and G2 are the same or different from each other and are each independently a substituted or unsubstituted cycloalkyl group; Or, it is a substituted or unsubstituted aryl group, or it forms a ring by combining with adjacent groups.

In one embodiment of the present specification, R7' is hydrogen; heavy hydrogen; Substituted or unsubstituted silyl group; Substituted or unsubstituted alkyl group; Or it is a substituted or unsubstituted aryl group.

According to an exemplary embodiment of the present specification, R7' is hydrogen; heavy hydrogen; A silyl group substituted or unsubstituted with one or more substituents or two or more substituents selected from the group consisting of an alkyl group, a halogen group, a cycloalkyl group, and an aryl group; an alkyl group substituted or unsubstituted with one or more substituents or two or more substituents selected from the group consisting of an alkyl group, a halogen group, a cycloalkyl group, and an aryl group; Or, it is a substituted or unsubstituted aryl group in which one or more substituents or two or more substituents selected from the group consisting of an alkyl group, a halogen group, a cycloalkyl group, and an aryl group are connected.

According to an exemplary embodiment of the present specification, R7' is hydrogen; heavy hydrogen; A silyl group substituted or unsubstituted with one or more substituents or two or more substituents selected from the group consisting of an alkyl group, a halogen group, a cycloalkyl group, and an aryl group; an alkyl group substituted or unsubstituted with one or more substituents or two or more substituents selected from the group consisting of an alkyl group, a halogen group, a cycloalkyl group, and an aryl group; Or, it is a substituted or unsubstituted aryl group in which one or more substituents or two or more substituents selected from the group consisting of an alkyl group, a halogen group, a cycloalkyl group, and an aryl group are connected.

According to an exemplary embodiment of the present specification, R7' is hydrogen; heavy hydrogen; an alkyl group having 1 to 10 carbon atoms; A silyl group substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms; Or, it is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, in which one or more substituents or two or more substituents selected from the group consisting of alkyl groups and silyl groups having 1 to 10 carbon atoms are linked.

According to an exemplary embodiment of the present specification, R7' is hydrogen; heavy hydrogen; methyl group; t-butyl group; trimethylsilyl group; Or it is a phenyl group substituted or unsubstituted with a trimethylsilyl group.

According to an exemplary embodiment of the present specification, R7' is hydrogen; methyl group; t-butyl group; trimethylsilyl group; Or it is a phenyl group substituted or unsubstituted with a trimethylsilyl group.

According to an exemplary embodiment of the present specification, R7' is hydrogen; methyl group; t-butyl group; trimethylsilyl group; Or it is a phenyl group substituted or unsubstituted with a trimethylsilyl group.

According to an exemplary embodiment of the present specification, R7' is represented by one of the following structural formulas.

In the above structural formula means the binding position.

According to an exemplary embodiment of the present specification, G1 and G2 are the same or different from each other, and are each independently a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; Or, it is a substituted or unsubstituted aryl group having 2 to 30 carbon atoms, or is bonded to adjacent groups to form a ring having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, G1 and G2 are the same or different from each other, and are each independently a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; Or, it is a substituted or unsubstituted aryl group having 2 to 20 carbon atoms, or is bonded to adjacent groups to form a ring having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, G1 and G2 are the same or different from each other, and are each independently a cycloalkyl group substituted or unsubstituted by an alkyl group or a halogen group; or an aryl group substituted or unsubstituted with an alkyl group or a halogen group, or a carbazole ring substituted or unsubstituted with an alkyl group or a halogen group by bonding to an adjacent group; Or, it forms a hexahydrocarbazole ring substituted or unsubstituted with an alkyl group or halogen group.

According to an exemplary embodiment of the present specification, G1 and G2 are the same as or different from each other, and are each independently a cycloalkyl group having 3 to 20 carbon atoms; or an aryl group with 6 to 20 carbon atoms substituted or unsubstituted with an alkyl group with 1 to 10 carbon atoms or a fluorine group, or a carbazole ring substituted or unsubstituted with an alkyl group with 1 to 10 carbon atoms by bonding to an adjacent group; Alternatively, it forms a substituted or unsubstituted hexahydrocarbazole ring with an alkyl group having 1 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, G1 and G2 are the same as or different from each other, and are each independently a cyclohexyl group; or a phenyl group substituted or unsubstituted with a methyl group, a t-butyl group, or a fluorine group, or a carbazole ring substituted or unsubstituted with a t-butyl group by bonding to an adjacent group; Or, it forms a hexahydrocarbazole ring substituted or unsubstituted with a methyl group.

According to an exemplary embodiment of the present specification, -N(G1)(G2) is represented by any of the following structural formulas.

In the above structural formula means the binding position.

According to an exemplary embodiment of the present specification, -N(G1)(G2) is represented by any of the following structural formulas.

In the above structural formula means the binding position.

In an exemplary embodiment of the present specification, Formula 2-1 is represented by the following Formula 2-1-1.

[Formula 2-1-1]

In the above formula 2-1-1,

The definitions of R7', R8 to R11, and r7 to r11 are the same as those in Formula 2-1 described above.

According to an exemplary embodiment of the present specification, in Formula 2, when r8 and r9 are 1, at least one of R8 and R9 is bonded to the ortho position from the position where N and the phenyl group are connected.

According to an exemplary embodiment of the present specification, in Formula 2, when r8 and r9 are 1, R8 and R9 are bonded to the ortho position from the position where N and the phenyl group are connected.

According to an exemplary embodiment of the present specification, in Formula 2, when r8 is 2 or more, at least one of the 2 or more R8 is bonded to the ortho position from the position where N and the phenyl group are connected.

According to an exemplary embodiment of the present specification, in Formula 2, when r9 is 2 or more, at least one of the 2 or more R9 is bonded to the ortho position from the position where N and the phenyl group are connected.

According to an exemplary embodiment of the present specification, the compound represented by Formula 2 has a left-right symmetrical structure with respect to the Z2 axis as shown in the following structural formula.

According to an exemplary embodiment of the present specification, the compound represented by Formula 2 has a left-right asymmetric structure with respect to the Z2 axis as shown in the structural formula below.

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

According to an exemplary embodiment of the present specification, the compound represented by Formula 2 is represented by any of the following structural formulas.

In the present invention, compounds 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 can be adjusted by introducing various substituents into the core structure of the above structure.

The compounds of formulas 1 and 2 of the present invention can be prepared with a core structure as shown in general formulas 1 and 2 below. Substituents may be combined by methods known in the art, and the type, position, and number of substituents may be changed according to techniques known in the art.

<General formula 1>

<General formula 2>

The definitions of the substituents are the same as those in Chemical Formulas 1 and 2.

The organic light-emitting device of the present invention can be manufactured using conventional organic light-emitting device manufacturing methods and materials, except that the light-emitting layer is formed using the compounds of Chemical Formulas 1 and 2 described above.

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

The organic light emitting device of the present invention may include one or more organic material layers between the first electrode and the second electrode.

The organic material layer of the organic light emitting device of the present invention may have a single-layer structure, or may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present invention includes one or more layers of a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron transport and injection layer as an organic material layer. It can have a structure that does. However, the structure of the organic light emitting device is not limited to this and may include fewer or more organic material layers.

The organic light-emitting device of the present invention includes a light-emitting layer, and the first organic material layer provided between the first electrode and the light-emitting layer includes a compound represented by Formula 1, and the light-emitting layer includes a compound represented by Formula 2.

According to one example, the thickness of the first organic material layer containing Formula 1 is 30Å to 300Å, and preferably 50Å to 200Å.

According to one example, the first organic material layer of the organic light emitting device of the present invention may be a hole transport layer or an electron blocking layer.

According to one example, the first organic material layer of the organic light-emitting device of the present invention includes an electron blocking layer, and the electron blocking layer includes the compound represented by Formula 1 above.

According to one example, the first organic material layer of the organic light-emitting device of the present invention is an electron blocking layer, and the electron blocking layer includes the compound represented by Formula 1 above.

According to one example, the light-emitting layer of the organic light-emitting device of the present invention includes a dopant, and the dopant is a compound represented by Formula 2 above.

According to one example, the first organic material layer of the organic light-emitting device of the present invention includes the compound represented by Formula 1 as a hole transport layer, and the light-emitting layer includes the compound represented by Formula 2 as a dopant of the light-emitting layer.

According to one example, the first organic layer of the organic light-emitting device of the present invention includes the compound represented by Formula 1 as an electron blocking layer, and the light-emitting layer includes the compound represented by Formula 2 as a dopant of the light-emitting layer.

In another embodiment, the first organic layer may further include other organic compounds, metals, or metal compounds in addition to the compound represented by Formula 1.

In another embodiment, the light-emitting layer may further include other organic compounds, metals, or metal compounds in addition to the compound represented by Formula 2.

In one embodiment of the present specification, based on 100 parts by weight of the compound represented by Formula 1, the content of the compound represented by Formula 2 is 0.01 parts by weight to 30 parts by weight; Preferably 0.1 to 20 parts by weight; More preferably, it is 0.5 parts by weight to 10 parts by weight. Organic light-emitting devices satisfying the above weight parts exhibit excellent characteristics in terms of driving voltage, luminous efficiency, or lifespan.

In one embodiment of the present specification, the light-emitting layer further includes a compound represented by the following formula H.

[Formula H]

In the formula H,

L21 to L23 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Ar21 to Ar23 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

m is 0 or 1.

In one embodiment of the present specification, when m is 0, hydrogen is connected to the position of -L23-Ar23.

In an exemplary embodiment of the present specification, L21 to L23 are the same or different from each other, and are each independently directly bonded; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, L21 to L23 are the same or different from each other, and are each independently directly bonded; phenylene group; Biphenylene group; naphthylene group; divalent dibenzofuran group; Or it is a divalent dibenzothiophene group.

In an exemplary embodiment of the present specification, Ar21 to Ar23 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In an exemplary embodiment of the present specification, Ar21 to Ar23 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, Ar21 to Ar23 are the same or different from each other, and each independently represents a substituted or unsubstituted monocyclic to tetracyclic aryl group; Or it is a substituted or unsubstituted monocyclic to tetracyclic heteroaryl group.

In an exemplary embodiment of the present specification, Ar21 to Ar23 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted anthracene group; Substituted or unsubstituted phenanthryl group; Substituted or unsubstituted phenalene group; Substituted or unsubstituted fluorenyl group; Substituted or unsubstituted benzofluorenyl group; Substituted or unsubstituted furan group; Substituted or unsubstituted thiophene group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted naphthobenzofuran group; Substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted naphthobenzothiophene group.

In an exemplary embodiment of the present specification, Ar21 to Ar23 are the same or different from each other, and are each independently a phenyl group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms; A biphenyl group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms; Naphthyl group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms; Dibenzofuran group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms; Naphthobenzofuran group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms; Dibenzothiophene group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms; Or it is a naphthobenzothiophene group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms.

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

An organic light-emitting device according to an embodiment of the present specification includes a light-emitting layer, and the light-emitting layer includes the compound represented by Formula 2 as a dopant of the light-emitting layer, and the compound represented by Formula H as a host of the light-emitting layer.

In one embodiment of the present specification, based on 100 parts by weight of the compound represented by Formula H, the content of the compound represented by Formula 2 is 0.01 parts by weight to 30 parts by weight; 0.1 to 20 parts by weight; Or 0.5 to 10 parts by weight.

In one embodiment of the present specification, the light-emitting layer may include one more host material in addition to the compound represented by Chemical Formula H. At this time, further included host materials (mixed host compounds) include condensed aromatic ring derivatives or heterocyclic ring-containing compounds. Specifically, condensed aromatic ring derivatives include pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds in addition to anthracene derivatives, and heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type compounds. There are furan compounds, pyrimidine derivatives, triazine derivatives, etc., and may be a mixture of two or more types thereof, but are not limited thereto.

The weight ratio of the compound represented by the formula H and the mixed host compound is 95:5 to 5:95, more preferably 30:70 to 70:30.

In an exemplary embodiment of the present specification, the light-emitting layer includes one or two or more types of compounds represented by the formula H.

In one embodiment of the present specification, the light-emitting layer including the compound represented by Formula 2 and the compound represented by Formula H has a blue color.

An organic light-emitting device according to an exemplary embodiment of the present specification includes two or more light-emitting layers, and at least one of the two or more light-emitting layers includes a compound represented by Formula 2 and a compound represented by Formula H. The light-emitting layer containing the compound represented by Formula 2 and the compound represented by Formula H has a blue color, and the light-emitting layer that does not contain the compound represented by Formula 2 and the compound represented by Formula H has a blue color known in the art. It may contain a red or green emitting compound.

In one embodiment of the present specification, the organic light-emitting device has a structure in which the first organic material layer and the light-emitting layer are adjacent to each other.

In the organic light emitting device of the present invention, the organic material layer may include a hole blocking layer, and the hole blocking layer may be made of materials known in the art.

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

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

The organic light emitting device may have, for example, a stacked structure as shown 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 blocking layer/light emitting layer/electron transport layer/cathode

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

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

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

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

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

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

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

In one embodiment of the present specification, the organic light emitting device may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

In one embodiment of the present specification, the organic light emitting device may be an inverted type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

The structure of the organic light emitting device of the present invention may have the same structure as shown in FIGS. 1 to 3, but is not limited thereto.

Figure 1 illustrates the structure of an organic light emitting device in which an anode 2, a light emitting layer 6, and a cathode 10 are sequentially stacked on a substrate 1. In this structure, the compound may be included in the light-emitting layer 6.

Figure 2 shows an organic light emitting device in which an anode (2), a hole injection layer (3), a hole transport layer (6), a light emitting layer (6), an electron transport layer (8), and a cathode (10) are sequentially stacked on a substrate (1). The structure is illustrated. In this structure, the compound may be included in the hole injection layer 3, the hole transport layer 6, the light emitting layer 6, or the electron transport layer 8.

Figure 3 shows an anode (2), a hole injection layer (3), a hole transport layer (4), an electron blocking layer (5), a light emitting layer (6), a hole blocking layer (7), and an electron transport layer (8) on a substrate (1). , shows an example of an organic light-emitting device consisting of an electron injection layer 9 and a cathode 10. In this structure, the compound is the hole injection layer (3), the hole transport layer (4), the electron blocking layer (5), the light emitting layer (6), the hole blocking layer (7), the electron transport layer (8) or the electron injection layer. It may be included in layer (9).

For example, the organic light emitting device according to the present invention deposits a metal, a conductive metal oxide, or an alloy thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation. Manufactured by depositing an anode, forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, an electron transport layer, and an electron injection layer thereon, and then depositing a material that can be used as a cathode thereon. It can be. In addition to this method, an organic light-emitting device can also be made by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

One or more organic layers are provided between the first electrode and the second electrode, and the organic layer includes a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, And it may further include one or more of the hole transport and injection layers.

The organic material layer may have a multi-layer structure including a hole injection layer, a hole transport layer, a layer that simultaneously performs electron injection and electron transport, an electron blocking layer, a light emitting layer and an electron transport layer, an electron injection layer, an electron transport and injection layer, etc., but is limited thereto. It may not be a single layer structure. In addition, the organic material layer uses a variety of polymer materials to form a smaller number of layers by using a solvent process rather than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. It can be manufactured in layers.

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

The cathode is an electrode that injects electrons, and the cathode material is preferably a material with a low work function to facilitate electron injection into the organic layer. Specific examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; There are multi-layer structure materials such as LiF/Al or LiO ₂ /Al, but they are not limited to these.

The hole injection layer is a layer that serves to facilitate the injection of holes from the anode to the light emitting layer, and the hole injection material is a material that can well inject holes from the anode at a low voltage. HOMO (highest occupied) of the hole injection material It is preferable that the molecular orbital is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrilehexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. organic substances, anthraquinone, polyaniline, and polythiophene series conductive polymers, etc., but are not limited to these. The thickness of the hole injection layer may be 1 to 150 nm. If the thickness of the hole injection layer is 1 nm or more, there is an advantage in preventing the hole injection characteristics from deteriorating, and if it 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 to preventing this.

The hole transport layer may play a role in facilitating the transport of holes. The hole transport material is a material that can transport holes from the anode or hole injection layer and transfer them to the light emitting layer, and a material with high mobility for holes is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers with both conjugated and non-conjugated portions, but are not limited to these.

An additional hole buffer layer may be provided between the hole injection layer and the hole transport layer, and may include hole injection or transport materials known in the art.

An electron blocking layer may be provided between the hole transport layer and the light emitting layer. The electron blocking layer may be made of the above-described compounds or materials known in the art.

In one embodiment of the present specification, the organic light emitting device may further include one or more light emitting layers in addition to the light emitting layer.

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

Host materials for the light-emitting layer include condensed aromatic ring derivatives or heterocycle-containing compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type compounds. These include, but are not limited to, furan compounds and pyrimidine derivatives.

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

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

The electron transport layer may play a role in facilitating the transport of electrons. The electron transport material is a material that can easily inject electrons from the cathode and transfer them to the light-emitting layer, and a material with high mobility for electrons is suitable. Specific examples include Al complex of 8-hydroxyquinoline; Complex containing Alq ₃ ; organic radical compounds; Hydroxyflavone-metal complexes, etc., but are not limited to these. The thickness of the electron transport layer may be 1 to 50 nm. If the thickness of the electron transport layer is 1 nm or more, there is an advantage in preventing the electron transport characteristics from deteriorating, and if it is 50 nm or less, the thickness of the electron transport layer is too thick to prevent the driving voltage from increasing to improve the movement of electrons. There are benefits to this.

The electron injection layer may serve to facilitate injection of electrons. The electron injection material has the ability to transport electrons, has an excellent electron injection effect from the cathode, a light emitting layer or a light emitting material, prevents movement of excitons generated in the light emitting layer to the hole injection layer, and also has an excellent electron injection effect from the cathode to the light emitting layer or light emitting material. , Compounds with excellent thin film forming ability are preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. and their derivatives, metals. These include, but are not limited to, complex compounds and nitrogen-containing five-membered ring derivatives.

Examples of the metal complex compounds 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, etc. It is not limited to this.

The hole blocking layer is a layer that prevents holes from reaching the cathode, and can generally be formed under the same conditions as the hole injection layer. Specifically, it includes oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complex, etc., but is not limited thereto.

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

Hereinafter, in order to explain the present specification in detail, examples will be given in detail. However, the embodiments according to the present specification may be modified in various other forms, and the scope of the present application is not to be construed as being limited to the embodiments described in detail below. The embodiments of this application are provided to more completely explain the present specification to those with average knowledge in the art.

Preparation Example 1: Preparation of Compound 1-1

Compound N,N-bis(4-bromophenyl)-[1,1'-biphenyl]-4-amine (9.50 g, 19.96 mmol) and phenanthrene-9-ylbo in a 500 ml round bottom flask under nitrogen atmosphere. After completely dissolving ronic acid (9.30 g, 41.91 mmol) in 240 ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (120 ml) was added, and tetrakis-(triphenylphosphine)palladium (0.69 g, 0.60 mmol) was added. It was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 250 ml of ethyl acetate to prepare Compound 1-1 (8.46 g, 63%).

MS[M+H] ⁺ = 674

Preparation Example 2: Preparation of Compound 1-2

Compound 4'-bromo-N-(4-bromophenyl)-N-phenyl-[1,1'-biphenyl]-4-amine (10.50 g, 22.06 mmol) in a 500 ml round bottom flask under nitrogen atmosphere. , Phenanthrene-9-ylboronic acid (10.28 g, 46.32 mmol) was completely dissolved in 240 ml of tetrahydrofuran, then 2M potassium carbonate aqueous solution (120 ml) was added, and tetrakis-(triphenylphosphine)palladium (0.76 g) was added. , 0.66 mmol) was added and then heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 220 ml of ethyl acetate to prepare Compound 1-2 (8.95 g, 60%).

MS[M+H] ⁺ = 674

Preparation Example 3: Preparation of Compound 1-3

Compound N-(3-bromophenyl)-N-(4-bromophenyl)-[1,1'-biphenyl]-4-amine (10.50 g, 22.06 mmol) in a 500 ml round bottom flask under nitrogen atmosphere. , phenanthrene-9-ylboronic acid (10.28g, 46.32 mmol) was completely dissolved in 240 ml of tetrahydrofuran, then 2M potassium carbonate aqueous solution (120 ml) was added, and tetrakis-(triphenylphosphine)palladium (0.7 6g) was added. , 0.66 mmol) was added and then heated and stirred for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 210 ml of ethyl acetate to prepare Compound 1-3 (9.24 g, 62%).

MS[M+H] ⁺ = 674

Preparation Example 4: Preparation of Compound 2-1

1) Synthesis of Intermediate A

10g (44mmol) of 1-bromo-2,3-dichlorobenzene was dissolved in 100mL of toluene, then diphenylamine (2.1eq, 92mmol), sodium t-butoxide (2.7eq, 120mmol), BTP (Bis(tri) -tert-butylphosphine)palladium(0)) (10 mol%) was added and stirred under reflux for 3 hours to synthesize intermediate A (2-chloro-N1,N1,N3,N3-tetraphenylbenzene-1,3-diamine). . The obtained intermediate A was purified using column chromatography.

Intermediate A: m/z=446.15 (C ₃₀ H ₂₃ ClN ₂ )

Yield=15g (75.8%), purity=99.5%

2) Synthesis of compound 2-1

Dissolve 10 g (22 mmol) of Intermediate A in 100 mL of t-butylbenzene and cool to -78°C. t-Butyllithium (2.0eq, 44mmol) was added and stirred for 6 hours. BBr ₃ (2.0eq, 44mmol) was added, stirred for 1 hour, and then raised to room temperature. Diisopropylethylamine (2.0eq, 44mmol) was slowly added dropwise at room temperature and stirred under reflux for 2 hours. After completion of the reaction, it was washed with KOAc aqueous solution and the organic layer was distilled under reduced pressure. The obtained solid was purified by recrystallization to obtain compound 2-1.

Compound 2-1: m/z=420.18 (C ₃₀ H ₂₁ BN ₂ )

Yield=7.5g (79.8%), purity=99.9%

Preparation Example 5: Preparation of Compound 2-2

1) Synthesis of intermediate B

Intermediate B was synthesized in the same manner as the synthesis of intermediate A in Preparation Example 4, except that bis(4-(t-butyl)phenyl)amine was used instead of diphenylamine in Preparation Example 4.

2) Synthesis of compound 2-2

Compound 2-2 was synthesized in the same manner as the synthesis of compound 2-1 in Preparation Example 4, except that Intermediate B was used instead of Intermediate A in Preparation Example 4.

Compound 2-2: m/z=644.43 (C ₄₆ H ₅₃ BN ₂ )

Yield=7.2g (75%), purity=99.8%

Preparation Example 6: Preparation of Compound 2-3

1) Synthesis of intermediate C

In Preparation Example 4, bis(4-(t-butyl)phenyl)amine was used instead of diphenylamine, and 1,5-dibromo-2,3-dichlorobenzene was used instead of 1-bromo-2,3-dichlorobenzene. Intermediate C was synthesized in the same manner as the synthesis of Intermediate A in Preparation Example 4, except that chlorobenzene was used.

2) Synthesis of Compound 2-3

Compound 2-3 was synthesized in the same manner as the synthesis of compound 2-1 in Preparation Example 4, except that Intermediate C was used instead of Intermediate A in Preparation Example 4.

Compound 2-3: m/z=924.18 (C ₆₆ H ₇₈ BN ₃ )

Yield=6.3g (62%), purity=99.8%

Comparative Example 1

A glass substrate coated with a thin film of ITO (indium tin oxide) with a thickness of 1,000 Å was placed in distilled water with a detergent dissolved in it and washed ultrasonically. At this time, a detergent manufactured by Fischer Co. was used, and distilled water filtered secondarily using a filter manufactured by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing with distilled water, it was ultrasonic washed with solvents of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Additionally, the substrate was cleaned for 5 minutes using oxygen plasma and then transported to a vacuum evaporator.

On the ITO transparent electrode prepared in this way, the following compound HI-1 and the following compound HI-2 were thermally vacuum deposited to a thickness of 100 Å at a ratio of 98:2 (molar ratio) to form a hole injection layer.

A hole transport layer was formed by vacuum depositing a compound (1150 Å) represented by the following formula HT-1, which is a hole transport material, on the hole injection layer.

Next, the following compound EB-1 was vacuum deposited on the hole transport layer to a film thickness of 50 Å to form an electron blocking layer.

Subsequently, a compound represented by the following formula BH-1 and a compound represented by the following formula BD-1 were vacuum deposited on the electron blocking layer to a film thickness of 200 Å at a weight ratio of 25:1 to form a light emitting layer.

A hole blocking layer was formed by vacuum depositing the following compound HB-1 to a film thickness of 50Å on the light emitting layer.

Next, the following compound ET-1 and the following compound LiQ (Lithium Quinolate) were vacuum deposited on the hole blocking layer at a weight ratio of 1:1 to form an electron transport layer with a thickness of 300 Å. Lithium fluoride (LiF) to a thickness of 12Å and aluminum to a thickness of 2,000Å were sequentially deposited on the electron transport layer to form an electron injection layer and a cathode, respectively.

In the above process, the deposition rate of organic matter was maintained at 0.4 ~ 0.7Å/sec, the deposition rate of lithium fluoride of the cathode was maintained at 0.3Å/sec, and aluminum was maintained at 2Å/sec, and the vacuum degree during deposition was 2x10 ^-7 ~ An organic light emitting device was manufactured by maintaining 5×10 ^-6 torr.

The compounds used in Comparative Example 1 are as follows.

Examples 1 to 9 and Comparative Examples 2 to 21

An organic light emitting device was manufactured in the same manner as Comparative Example 1, except that the compounds listed in Table 1 below were used instead of the electron blocking layer compound EB-1 and the dopant compound BD-1. The compounds used in the above examples and comparative examples are as follows.

Experiment example

When a current of 20 mA/cm ² was applied to the organic light-emitting device manufactured in the Examples and Comparative Examples, the driving voltage, luminous efficiency, and color coordinates of the organic light-emitting device were changed at a current density of 20 mA/cm ² The time for reaching 95% of the initial luminance (T95) was measured at a current density of 20 mA/cm ² . The results are shown in Table 1 below. T95 refers to the time it takes for the luminance to decrease from the initial luminance (1600 nit) to 95%.

compound
(electron blocking layer) compound
(dopant) Voltage
(V
@20mA
/cm ² ) efficiency
(cd/A
@20mA
/cm ² ) Color coordinates
(x,y) T95
(hr) Example 1 1-1 2-1 3.65 6.89 (0.144, 0.045) 360 Example 2 1-2 2-1 3.77 6.74 (0.146, 0.046) 345 Example 3 1-3 2-1 3.83 6.63 (0.145, 0.047) 355 Example 4 1-1 2-2 3.64 6.82 (0.147, 0.046) 365 Example 5 1-2 2-2 3.76 6.73 (0.146, 0.048) 340 Example 6 1-3 2-2 3.82 6.65 (0.145, 0.047) 335 Example 7 1-1 2-3 3.67 6.80 (0.146, 0.045) 360 Example 8 1-2 2-3 3.73 6.74 (0.147, 0.046) 345 Example 9 1-3 2-3 3.82 6.61 (0.145, 0.048) 330 Comparative Example 1 EB-1 BD-1 4.26 5.82 (0.147, 0.155) 245 Comparative Example 2 1-1 BD-1 4.05 6.07 (0.146, 0.156) 260 Comparative Example 3 1-2 BD-1 4.02 6.00 (0.145, 0.159) 265 Comparative Example 4 1-3 BD-1 4.08 6.03 (0.147, 0.155) 265 Comparative Example 5 EB-1 2-1 4.18 6.28 (0.146, 0.047) 330 Comparative Example 6 EB-1 2-2 4.14 6.22 (0.144, 0.048) 315 Comparative Example 7 EB-1 2-3 4.16 6.24 (0.145, 0.046) 305 Comparative Example 8 EB-2 2-1 3.92 6.56 (0.146, 0.046) 270 Comparative Example 9 EB-2 2-2 3.93 6.41 (0.144, 0.047) 270 Comparative Example 10 EB-2 2-3 3.96 6.47 (0.144, 0.048) 275 Comparative Example 11 EB-3 2-1 3.82 6.49 (0.145, 0.047) 290 Comparative Example 12 EB-3 2-2 3.80 6.53 (0.144, 0.047) 250 Comparative Example 13 EB-3 2-3 3.83 6.41 (0.146, 0.048) 285 Comparative Example 14 EB-2 BD-1 4.12 6.11 (0.146, 0.158) 285 Comparative Example 15 EB-3 BD-1 4.03 6.23 (0.146, 0.158) 285 Comparative Example 16 1-1 BD-2 4.71 5.62 (0.146, 0.153) 265 Comparative Example 17 1-2 BD-2 4.68 5.58 (0.147, 0.152) 265 Comparative Example 18 1-3 BD-2 4.72 5.64 (0.145, 0.153) 265 Comparative Example 19 EB-4 2-1 4.42 5.89 (0.145, 0.041) 270 Comparative Example 20 EB-4 2-2 4.38 5.92 (0.144, 0.042) 235 Comparative Example 21 EB-4 2-3 4.37 5.94 (0.144, 0.043) 260

As shown in Table 1, the organic light-emitting device of the example in which the compound represented by Formula 1 is used as an electron blocking layer material and the compound represented by Formula 2 is simultaneously used as a dopant material of the light-emitting layer, Formulas 1 and 2 Compared to the organic light-emitting devices of Comparative Examples 2 to 13 and 16 to 21 employing one of the compounds represented by , excellent characteristics were exhibited in terms of driving voltage, luminous efficiency and lifespan.

It was confirmed that the efficiency and lifespan characteristics of the organic light-emitting device of an embodiment according to the present invention employing both the compound represented by Formula 1 and the compound represented by Formula 2 were improved at the same time. Considering that the luminous efficiency and lifespan characteristics of organic light-emitting devices generally have a trade-off relationship, organic light-emitting devices employing a combination of compounds of the present invention have significantly improved device characteristics compared to comparative devices. It can be seen that it represents .

1: substrate
2: anode
3: Hole injection layer
4: Hole transport layer
5: Electronic blocking layer
6: Light-emitting layer
7: Hole blocking layer
8: Electron transport layer
9: Electron injection layer
10: cathode

Claims (14)

first electrode;
second electrode;
a light emitting layer provided between the first electrode and the second electrode; and
In the organic light-emitting device comprising a first organic material layer provided between the first electrode and the light-emitting layer,
The first organic layer includes a compound represented by the following formula (1),
An organic light-emitting device wherein the light-emitting layer includes a compound represented by the following formula (2):
[Formula 1]

In Formula 1,
Ar1 is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
L1 to L3 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted alkylene group; Substituted or unsubstituted arylene group; A substituted or unsubstituted divalent alkoxy group; A substituted or unsubstituted divalent alkenyl group; Or a substituted or unsubstituted divalent heterocyclic group,
R1 to R6 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Nitrile group; Substituted or unsubstituted silyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
r1 to r4 are the same or different from each other and are each independently an integer of 0 to 4,
When r1 to r4 are integers of 2 or more, the substituents in parentheses are the same or different from each other,
[Formula 2]

In Formula 2,
R7 to R11 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Nitrile group; Substituted or unsubstituted amine group; Substituted or unsubstituted silyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
r7 is an integer from 1 to 3,
r8 and r9 are the same or different from each other and are each independently an integer of 1 to 5,
r10 and r11 are the same or different from each other and are each independently an integer of 1 to 4,
When r7 to r11 are integers of 2 or more, the substituents in parentheses are the same or different from each other. In claim 1,
Ar1 is a substituted or unsubstituted phenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted triphenylenyl group; Substituted or unsubstituted fluorenyl group; Or an organic light-emitting device that is a substituted or unsubstituted spirobifluorenyl group. In claim 1,
The organic light-emitting device wherein Ar1 is represented by any of the following formulas:


In the above formula,
R is hydrogen; heavy hydrogen; halogen group; Nitrile group; Substituted or unsubstituted silyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
The dotted line indicates the binding site where L1 is bound. In claim 1,
wherein L1 to L3 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted phenylene group; Substituted or unsubstituted naphthylene group; Substituted or unsubstituted biphenylene group; Substituted or unsubstituted terphenylene group; Substituted or unsubstituted phenanthrenylene group; Substituted or unsubstituted triphenylenylene group; Or an organic light-emitting device that is a substituted or unsubstituted fluorenylene group. In claim 1,
An organic light emitting device wherein L1 to L3 are a direct bond or are represented by any of the following formulas:

In the above formula,
R' and R'' are hydrogen; heavy hydrogen; halogen group; Nitrile group; Substituted or unsubstituted silyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
The dotted line indicates the binding position. The organic light emitting device according to claim 1, wherein R1 to R4 are hydrogen. The method according to claim 1, wherein R7 to R11 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Substituted or unsubstituted amine group; Substituted or unsubstituted silyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted pyridyl group; Substituted or unsubstituted carbazole group; Or an organic light-emitting device that is a substituted or unsubstituted hexahydrocarbazole group. The organic light-emitting device according to claim 1, wherein the compound represented by Formula 1 is represented by any one of the following structural formulas:





. The organic light-emitting device according to claim 1, wherein the compound represented by Formula 2 is represented by any of the following structural formulas:









. In claim 1,
An organic light emitting device wherein the first organic material layer includes an electron blocking layer, and the electron blocking layer includes a compound represented by Formula 1. In claim 1,
An organic light-emitting device wherein the light-emitting layer includes a dopant, and the dopant includes a compound represented by Formula 2. In claim 1,
An organic light-emitting device wherein the thickness of the first organic material layer containing Formula 1 is 50Å to 200Å. In claim 1,
An organic light-emitting device wherein the light-emitting layer further includes a compound represented by the following formula H:
[Formula H]

In the formula H,
L21 to L23 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar21 to Ar23 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
m is 0 or 1. In claim 1,
One or more organic layers are provided between the first electrode and the second electrode, and the organic layer includes a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an organic light emitting device further comprising at least one of a hole transport and injection layer.