KR102594848B1 - Organic light emitting device - Google Patents

Abstract

This specification includes: a first electrode; second electrode; and an organic light-emitting device comprising an organic material layer provided between the first electrode and the second electrode, wherein the organic material layer includes a light-emitting layer, and the light-emitting layer includes a compound represented by Formula 1 and a compound represented by Formula 2. An organic light emitting device is provided.

Description

Organic light emitting device {ORGANIC LIGHT EMITTING DEVICE}

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 disappear, 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 use, 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.

WO 2017-175690

In this specification, an organic light emitting device with long lifespan characteristics is provided.

One embodiment of this specification is

first electrode;

second electrode;

And an organic light emitting device comprising an organic material layer provided between the first electrode and the second electrode,

The organic layer includes a light-emitting layer,

The light emitting layer provides an organic light emitting device comprising a compound represented by Formula 1 below and a compound represented by Formula 2 below.

[Formula 1]

In Formula 1,

Ar1 and Ar2 are the same or different from each other, and are each independently deuterium; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

Ar3 is hydrogen; heavy hydrogen; 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 arylene group; Or a substituted or unsubstituted divalent heterocyclic group,

R1 is hydrogen; heavy hydrogen; halogen group; Nitrile group; Substituted or unsubstituted silyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted thioalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryl group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted aralkyl group; Or it is a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,

a to c are integers from 0 to 3, and when a to c is 2 or more, the substituents in parentheses are the same or different from each other,

r1 is an integer from 0 to 7, and when r1 is 2 or more, R1 is the same as or different from each other,

The compound represented by Formula 1 contains at least one deuterium,

[Formula 2]

In Formula 2,

A to C are the same or different from each other, and each independently represents a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted heterocycle,

At least one of A to C is a ring having two or more rings.

The organic light emitting device of the present invention simultaneously contains the compound represented by Formula 1 and the compound represented by Formula 2, thereby making it possible to obtain an organic light emitting device having a long lifespan.

1 to 3 show examples of organic light-emitting devices according to an exemplary embodiment of the present specification.
4 and 5 show examples of organic light-emitting devices including two or more stacks.

Hereinafter, this specification will be described in more detail.

This specification

first electrode;

second electrode;

And an organic light emitting device comprising an organic material layer provided between the first electrode and the second electrode,

The organic layer includes a light-emitting layer,

The light emitting layer provides an organic light emitting device including a compound represented by Formula 1 and a compound represented by Formula 2.

In Formula 1, hydrogen, deuterium, an aryl group, or a heterocyclic group are connected to carbons 2, 9, and 10 of anthracene. In addition, Formula 1 contains one or more deuterium, improving the efficiency and lifespan of the device. Specifically, when hydrogen is replaced with deuterium, the chemical properties of the compound rarely change. However, since the atomic weight of deuterium is twice that of hydrogen, the physical properties of deuterated compounds may change. For example, compounds substituted with deuterium have a lower vibrational energy level. Compounds substituted with deuterium can prevent a decrease in quantum efficiency due to a decrease in intermolecular van der Waals forces or collisions due to intermolecular vibrations. Additionally, C-D bonds can improve the stability of compounds. Accordingly, the compound represented by Formula 1 can improve the efficiency and lifespan of the device by containing deuterium.

The compound of Formula 1 containing deuterium can be prepared by a known deuteration reaction. According to an exemplary embodiment of the present specification, the compound represented by Formula 1 is formed by using a deuterated compound as a precursor, or by introducing deuterium into the compound through a hydrogen-deuterium exchange reaction under an acid catalyst using a deuterated solvent. You may.

Formula 2 is a structure in which an aromatic hydrocarbon ring or heterocycle is condensed around N, and at least one of the rings consists of two or more rings.

When combining the above-mentioned formula 1 and the above-mentioned formula 2, an organic light-emitting device is produced that has the effect of improving lifespan due to enthalpy stability of deuterium while maintaining Forster-energy transfer, in which energy is transferred from the host to the dopant. You can get it.

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, the “layer” is interchangeable with the “film” mainly used in the present technical field, and refers to a coating that covers the target area. The size of the 'layer' is not limited, and each 'layer' may have the same or different size. In one embodiment, the size of a 'layer' may be the same as the entire device, may correspond to the size of a specific functional area, or may be as small as a single sub-pixel.

In this specification, the inclusion of a specific material A in the layer B means that i) one or more types of material A are included in one layer B, and ii) the layer B consists of one or more layers, and the material A is included in a multi-layer B. Includes everything on the first or higher floors.

In this specification, the meaning that a specific material A is included in the C layer or D layer means that it is i) included in one or more layers of one or more layers of C, ii) included in one or more layers of one or more layers of D, or iii ) This means that it is included in each of the C floors above the first floor and the D floors above the first floor.

In this specification, N% substitution with deuterium means that N% of the hydrogen available in the structure is replaced with deuterium. For example, if 25% of dibenzofuran is replaced with deuterium, it means that 2 of the 8 hydrogens in dibenzofuran are replaced with deuterium.

In this specification, the degree of deuteration can be confirmed by known methods such as nuclear magnetic resonance spectroscopy ( ^1H NMR) or GC/MS.

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; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; and substituted or unsubstituted heterocyclic groups, 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.

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 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, except for the divalent group.

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

The description of the heterocyclic group can be applied, except that the heterocyclic ring is divalent.

An exemplary embodiment of the present specification includes a first electrode; second electrode; and an organic light-emitting device comprising an organic material layer provided between the first electrode and the second electrode, wherein the organic material layer includes a light-emitting layer, and the light-emitting layer includes a compound represented by Formula 1 below and a compound represented by Formula 2 below. It provides an organic light emitting device comprising a.

[Formula 1]

In Formula 1,

Ar1 and Ar2 are the same or different from each other, and are each independently deuterium; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

Ar3 is hydrogen; heavy hydrogen; 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 arylene group; Or a substituted or unsubstituted divalent heterocyclic group,

R1 is hydrogen; heavy hydrogen; halogen group; Nitrile group; Substituted or unsubstituted silyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted thioalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryl group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted aralkyl group; Or it is a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,

a to c are integers from 0 to 3, and when a to c is 2 or more, the substituents in parentheses are the same or different from each other,

r1 is an integer from 0 to 7, and when r1 is 2 or more, R1 is the same as or different from each other,

The compound represented by Formula 1 contains at least one deuterium,

[Formula 2]

In Formula 2,

A to C are the same or different from each other, and each independently represents a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted heterocycle,

At least one of A to C is a ring having two or more rings.

Hereinafter, Chemical Formula 1 of the present specification will be described in detail.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently deuterium; Substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heterocyclic group.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heterocyclic group.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently 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.

In an exemplary embodiment of the present specification, Ar1 and Ar2 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 heterocyclic group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same or different from each other, and are each independently a substituted or unsubstituted phenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted anthracenyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted naphthobenzofuran group; Or a substituted or unsubstituted naphthobenzothiophene group.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same or different from each other, and are each independently a phenyl group substituted or unsubstituted with deuterium; Naphthyl group substituted or unsubstituted with deuterium; Biphenyl group substituted or unsubstituted with deuterium; Anthracenyl group substituted or unsubstituted with deuterium; A phenanthrenyl group substituted or unsubstituted with deuterium; Dibenzofuran group substituted or unsubstituted with deuterium or phenyl group; Dibenzothiophene group substituted or unsubstituted with deuterium; Naphthobenzofuran group substituted or unsubstituted with deuterium; Or it is a naphthobenzothiophene group substituted or unsubstituted with deuterium.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same or different from each other, and are each independently a phenyl group substituted or unsubstituted with deuterium; Naphthyl group substituted or unsubstituted with deuterium; Biphenyl group substituted or unsubstituted with deuterium; A phenanthrenyl group substituted or unsubstituted with deuterium; Dibenzofuran group substituted or unsubstituted with deuterium or phenyl group; Or it is a naphthobenzofuran group substituted or unsubstituted with deuterium.

In one embodiment of the present specification, Ar3 is hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, Ar3 is hydrogen; heavy hydrogen; 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.

In one embodiment of the present specification, Ar3 is hydrogen; heavy hydrogen; 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.

In one embodiment of the present specification, Ar3 is hydrogen; heavy hydrogen; Substituted or unsubstituted phenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.

In one embodiment of the present specification, Ar3 is hydrogen; heavy hydrogen; A phenyl group substituted or unsubstituted with deuterium; Naphthyl group substituted or unsubstituted with deuterium; Biphenyl group substituted or unsubstituted with deuterium; A phenanthrenyl group substituted or unsubstituted with deuterium; Dibenzofuran group substituted or unsubstituted with deuterium; Or it is a dibenzothiophene group substituted or unsubstituted with deuterium.

In one embodiment of the present specification, Ar3 is hydrogen; heavy hydrogen; A phenyl group substituted or unsubstituted with deuterium; Naphthyl group substituted or unsubstituted with deuterium; Biphenyl group substituted or unsubstituted with deuterium; A phenanthrenyl group substituted or unsubstituted with deuterium; Or it is a dibenzofuran group substituted or unsubstituted with deuterium.

In an exemplary embodiment of the present specification, L1 to L3 are the same 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.

In an exemplary embodiment of the present specification, L1 to L3 are the same or different from each other and are each independently directly bonded; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or it is a substituted or unsubstituted divalent heterocyclic group having 2 to 60 carbon atoms.

In an exemplary embodiment of the present specification, L1 to L3 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 divalent heterocyclic group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, L1 to L3 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted phenylene group; Or a substituted or unsubstituted dibenzofuran group.

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

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

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

According to an exemplary embodiment of the present specification, L1 to L3 are directly bonded; Or, it is displayed as shown below.

In the above structures, d1 is an integer from 0 to 4, and d2 is an integer from 0 to 6.

In one embodiment of the present specification, R1 is hydrogen; heavy hydrogen; halogen group; Nitrile group; Substituted or unsubstituted silyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted thioalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryl group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted aralkyl group; Or, it is a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted ring.

In one embodiment of the present specification, R1 is hydrogen; Or deuterium.

In one embodiment of the present specification, a to c are integers from 0 to 3, and when a to c are 2 or more, the substituents in parentheses are the same as or different from each other.

In one embodiment of the present specification, a to c are 1 or 2.

In one embodiment of the present specification, r1 is an integer from 0 to 7, and when r1 is 2 or more, R1 is the same as or different from each other.

In an exemplary embodiment of the present specification, the compound represented by Formula 1 includes at least one deuterium.

In one embodiment of the present specification, the compound represented by Formula 1 is substituted by more than 30% with deuterium. In another exemplary embodiment, the compound represented by Formula 1 is substituted by more than 40% with deuterium. In another exemplary embodiment, the compound represented by Formula 1 is substituted by more than 50% with deuterium. In another exemplary embodiment, the compound represented by Formula 1 is substituted by more than 60% with deuterium. In another exemplary embodiment, the compound represented by Formula 1 is substituted by more than 70% with deuterium. In another exemplary embodiment, the compound represented by Formula 1 is substituted by more than 80% with deuterium. In another exemplary embodiment, the compound represented by Formula 1 is substituted by more than 90% with deuterium. In another exemplary embodiment, the compound represented by Formula 1 is 100% substituted with deuterium.

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

In the above structural formula, v, w, x, y and z mean the substitution rate (%) of deuterium (D) compared to the total hydrogen that can be substituted in the structural formula,

v+w+x+y+z is 40% to 100%.

According to an exemplary embodiment of the present specification, v+w+x+y+z is 50% to 100%.

According to an exemplary embodiment of the present specification, v+w+x+y+z is 60% to 100%.

According to an exemplary embodiment of the present specification, v+w+x+y+z is 70% to 100%.

According to an exemplary embodiment of the present specification, v+w+x+y+z is 80% to 100%.

According to an exemplary embodiment of the present specification, v+w+x+y+z is 90% to 100%.

Hereinafter, Chemical Formula 2 of the present specification will be described in detail.

In an exemplary embodiment of the present specification, A to C are the same or different from each other, and each independently represents a substituted or unsubstituted aromatic hydrocarbon ring; Or it is a substituted or unsubstituted heterocycle.

In an exemplary embodiment of the present specification, A to C are the same or different from each other, and each independently represents a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms; Or it is a substituted or unsubstituted heterocycle having 2 to 60 carbon atoms.

In an exemplary embodiment of the present specification, A to C are the same or different from each other, and each independently represents a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted heterocycle having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, A to C are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic to hexacyclic aromatic hydrocarbon ring; Or it is a substituted or unsubstituted mono- to 6-ring heterocycle.

In an exemplary embodiment of the present specification, A to C are the same or different from each other, and each independently represents a substituted or unsubstituted monocyclic to tetracyclic aromatic hydrocarbon ring; Or it is a substituted or unsubstituted monocyclic to tetracyclic heterocycle.

In an exemplary embodiment of the present specification, A to C are the same or different from each other, and each independently represents a substituted or unsubstituted monocyclic to tricyclic aromatic hydrocarbon ring; Or it is a substituted or unsubstituted monocyclic to tricyclic heterocycle.

In one embodiment of the present specification, A is a substituted or unsubstituted monocyclic to tricyclic aromatic hydrocarbon ring; Or it is a substituted or unsubstituted monocyclic to tricyclic heterocycle.

In one embodiment of the present specification, A is a substituted or unsubstituted benzene ring; Substituted or unsubstituted naphthalene ring; Substituted or unsubstituted fluorene ring; A substituted or unsubstituted spirobifluorene ring; Substituted or unsubstituted anthracene ring; Substituted or unsubstituted phenanthrene ring; Substituted or unsubstituted pyrene ring; Substituted or unsubstituted carbazole ring; Substituted or unsubstituted dibenzofuran ring; Or a substituted or unsubstituted dibenzothiophene ring.

In one embodiment of the present specification, A is a benzene ring substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 20 carbon atoms; A naphthalene ring substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 20 carbon atoms; A fluorene ring unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 20 carbon atoms; A spirobifluorene ring substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 20 carbon atoms; An anthracene ring unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 20 carbon atoms; A phenanthrene ring substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 20 carbon atoms; A pyrene ring unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 20 carbon atoms; A carbazole ring substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 20 carbon atoms; A dibenzofuran ring substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 20 carbon atoms; Or it is a dibenzothiophene ring substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, A is a benzene ring; naphthalene ring; A fluorene ring substituted or unsubstituted with a methyl group; Spirobifluorene ring; anthracene ring; phenanthrene ring; pyrene ring; Carbazole ring substituted or unsubstituted with a phenyl group; Dibenzofuran ring; Or it is a dibenzothiophene ring.

In one embodiment of the present specification, A is a benzene ring; naphthalene ring; 9,9-dimethylfluorene ring; 9,9'-spirobifluorene ring; anthracene ring; phenanthrene ring; pyrene ring; 9-phenyl-carbazole ring; Dibenzofuran ring; Or it is a dibenzothiophene ring.

In an exemplary embodiment of the present specification, B and C are the same or different from each other, and each independently represents a substituted or unsubstituted monocyclic to tetracyclic aromatic hydrocarbon ring; Or it is a substituted or unsubstituted monocyclic to tricyclic heterocycle.

In an exemplary embodiment of the present specification, B and C are the same or different from each other, and are each independently a substituted or unsubstituted benzene ring; Substituted or unsubstituted naphthalene ring; Substituted or unsubstituted fluorene ring; A substituted or unsubstituted benzofluorene ring; Substituted or unsubstituted anthracene ring; Substituted or unsubstituted phenanthrene ring; Substituted or unsubstituted pyrene ring; A substituted or unsubstituted spirobifluorene ring; Substituted or unsubstituted carbazole ring; Substituted or unsubstituted dibenzofuran ring; Or a substituted or unsubstituted dibenzothiophene ring.

In an exemplary embodiment of the present specification, B and C are the same or different from each other, and are each independently substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an arylamine group having 6 to 20 carbon atoms. benzene ring; A naphthalene ring substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an arylamine group having 6 to 20 carbon atoms; A fluorene ring unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an arylamine group having 6 to 20 carbon atoms; A benzofluorene ring substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an arylamine group having 6 to 20 carbon atoms; An anthracene ring unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an arylamine group having 6 to 20 carbon atoms; A phenanthrene ring unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an arylamine group having 6 to 20 carbon atoms; A pyrene ring unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an arylamine group having 6 to 20 carbon atoms; A spirobifluorene ring unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an arylamine group having 6 to 20 carbon atoms; A carbazole ring substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an arylamine group having 6 to 20 carbon atoms; A dibenzofuran ring unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an arylamine group having 6 to 20 carbon atoms; Or it is a dibenzothiophene ring substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an arylamine group having 6 to 20 carbon atoms.

In an exemplary embodiment of the present specification, B and C are the same or different from each other, and are each independently a benzene ring; A naphthalene ring substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms; A fluorene ring substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms or an arylamine group having 6 to 20 carbon atoms; A benzofluorene ring substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms; Spirobifluorene ring; A carbazole ring substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms or an arylamine group having 6 to 20 carbon atoms; A dibenzofuran ring substituted or unsubstituted with an arylamine group having 6 to 20 carbon atoms; Or it is a dibenzothiophene ring substituted or unsubstituted with an arylamine group having 6 to 20 carbon atoms.

In an exemplary embodiment of the present specification, B and C are the same or different from each other, and are each independently a benzene ring; A naphthalene ring substituted or unsubstituted with an i-propyl group or t-butyl group; A fluorene ring substituted or unsubstituted with one or more amine groups substituted with a methyl group or a phenyl group; A benzofluorene ring substituted or unsubstituted with a methyl group; Spirobifluorene ring; A carbazole ring substituted or unsubstituted with at least one phenyl group and an amine group substituted with a phenyl group; A dibenzofuran ring substituted or unsubstituted with an amine group substituted with a phenyl group; Or it is a dibenzothiophene ring substituted or unsubstituted with an amine group substituted with a phenyl group.

In an exemplary embodiment of the present specification, at least one of A to C is a two or more ring ring.

In one embodiment of the present specification, A is a ring of two or more rings.

In one embodiment of the present specification, B is a ring of two or more rings.

In one embodiment of the present specification, C is a ring of two or more rings.

In one embodiment of the present specification, A and B are two or more rings.

In one embodiment of the present specification, A and C are two or more rings.

In one embodiment of the present specification, B and C are two or more rings.

In an exemplary embodiment of the present specification, A to C are two or more rings.

In an exemplary embodiment of the present specification, at least one of B and C is represented by any one of the following formulas 3 to 7.

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

In Formulas 3 to 7, * refers to the condensation position,

X is NRa; O; S; or CRbRc,

Ra to Rc are the same or different from each other, and are each independently a substituted or unsubstituted alkyl group; It is a substituted or unsubstituted aryl group, or combines with an adjacent group to form a substituted or unsubstituted ring,

G1 and G11 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 cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,

g1 and g11 are integers from 0 to 6, and when g1 and g11 are 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 Formula 2-2.

[Formula 2-1]

[Formula 2-2]

In Formulas 2-1 and 2-2, the definition of A is the same as the definition in Formula 2,

X and Y are the same or different from each other and are each independently NRa; O; S; or CRbRc,

Ra to Rc are the same or different from each other, and are each independently a substituted or unsubstituted alkyl group; It is a substituted or unsubstituted aryl group, or combines with an adjacent group to form a substituted or unsubstituted ring,

G1 to G4 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 cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,

n is 0 to 2,

g1 and g2 are the same as or different from each other, and are each independently an integer of 0 to 6, and when g1 and g2 are 2 or more, the substituents in parentheses are the same or different from each other,

g4 is an integer from 0 to 4, and when g4 is 2 or more, G4 is the same as or different from each other,

g3 is an integer from 0 to 2, and when g3 is 2, G3 are the same or different from each other.

In an exemplary embodiment of the present specification, Ra to Rc are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; It is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or is bonded to an adjacent group to form a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In an exemplary embodiment of the present specification, Ra to Rc are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms; It is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or is bonded to an adjacent group to form a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In an exemplary embodiment of the present specification, Ra to Rc are the same or different from each other, and are each independently a methyl group; Or, it is a phenyl group, or combines with adjacent groups to form a fluorene ring.

In an exemplary embodiment of the present specification, G1 to G4 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 60 carbon atoms; Or, it is a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms, or adjacent groups are combined with each other to form a substituted or unsubstituted ring having 6 to 30 carbon atoms.

In an exemplary embodiment of the present specification, G1 to G4 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 15 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, or adjacent groups are combined with each other to form a substituted or unsubstituted ring having 6 to 15 carbon atoms.

In an exemplary embodiment of the present specification, G1 to G4 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; It is an amine group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms, or adjacent groups are combined with each other to form a substituted or unsubstituted benzene ring.

In an exemplary embodiment of the present specification, G1 to G4 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; It is an amine group substituted or unsubstituted by a phenyl group, or adjacent groups are combined with each other to form a benzene ring.

In one embodiment of the present specification, n is 0.

In one embodiment of the present specification, n is 1.

In an exemplary embodiment of the present specification, g1 and g2 are 1 or 2.

In an exemplary embodiment of the present specification, Formula 2-1 is represented by any one of the following Formulas 2-1-1 to 2-1-9.

[Formula 2-1-1]

[Formula 2-1-2]

[Formula 2-1-3]

[Formula 2-1-4]

[Formula 2-1-5]

[Formula 2-1-6]

[Formula 2-1-7]

[Formula 2-1-8]

[Formula 2-1-9]

In the above formulas 2-1-1 to 2-1-9,

The definition of the substituent is the same as that in Chemical Formula 2-1.

In an exemplary embodiment of the present specification, Formula 2-2 is represented by any one of the following Formulas 2-2-1 to 2-2-4.

[Formula 2-2-1]

[Formula 2-2-2]

[Formula 2-2-3]

[Formula 2-2-4]

In the above formulas 2-2-1 to 2-2-4,

The definition of the substituent is the same as that in Chemical Formula 2-2.

According to an exemplary embodiment of the present specification, the compound represented by Formula 2 is represented by one of the following compounds.

According to an exemplary embodiment of the present specification, the compound of Formula 1 may be prepared according to Scheme 1 to Scheme 3 below, but is not limited thereto. Additionally, compounds prepared according to Schemes 1 and 2 may be substituted with deuterium through the same process as Scheme 3. At this time, the deuterium substitution rate in Scheme 3 is 40% to 100%. In Schemes 1 to 3 below, the type and number of substituents can be determined by those skilled in the art by appropriately selecting known starting materials. Reaction types and reaction conditions may be those known in the art.

[Scheme 1]

[Scheme 2]

[Scheme 3]

The level of deuteration of a compound according to an exemplary embodiment of the present specification can be determined by NMR analysis or mass spectrometry.

Hereinafter, the organic light emitting device will be described.

In an exemplary embodiment of the present specification, the organic material layer of the organic light-emitting device further includes two or more types of compounds, a compound represented by Formula 1 excluding the compound represented by Formula 2, and a triplet of the two or more types of compounds The energy (T _org ) is 2.5 eV or more, and the triplet energy (T _org ) of the compound represented by Formula 1 and at least 3 types of the two or more compounds is 2.7 eV or more. At this time, the compound represented by Formula 2 may act as a light-emitting dopant, and the Forster energy transfer efficiency of the two or more types of compounds to the light-emitting dopant may be 90% or more due to the energy barrier, but is limited to this. It doesn't work.

In one embodiment of the present specification, the organic material layer of the organic light-emitting device further includes two or more types of compounds, and the organic material layer includes a hole injection layer, a hole transport layer, a layer that simultaneously performs hole transport and hole injection, an electron blocking layer, and a light emitting layer. , it may include an electron transport layer, an electron injection layer, a layer that simultaneously performs electron transport and electron injection, or a hole blocking layer. That is, the above two or more compounds are a hole injection layer, a hole transport layer, a layer that simultaneously performs hole transport and hole injection, an electron blocking layer, a light-emitting layer, an electron transport layer, an electron injection layer, a layer that simultaneously performs electron transport and electron injection, or a hole blocking layer. It may be a compound included in the layer.

In this specification, triplet energy can be measured using a spectroscopic instrument capable of measuring fluorescence and phosphorescence, and in the case of measurement conditions, at a concentration of 10 ^-6 M using toluene or THF as a solvent in a cryogenic state using liquid nitrogen. Prepare a solution, irradiate the solution with a light source in the absorption wavelength range of the material, exclude singlet emission from the emission spectrum, and analyze and confirm the spectrum of triplet emission. When electrons are reversed from a light source, the time the electrons stay in a triplet is much longer than the time they stay in a singlet, so separation of the two components is possible at extremely low temperatures.

The organic light-emitting device of the present invention can be manufactured by conventional organic light-emitting device manufacturing methods and materials, except that the organic material layer is formed using the compound represented by the above-mentioned formula 1 and the compound represented by the above-mentioned formula 2. You can.

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

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 material layer of the organic light emitting device of the present specification may have a structure that includes only the organic material layer, or may have a structure that further includes an additional organic material layer. As the additional organic layer, one of a hole injection layer, a hole transport layer, a layer that simultaneously performs hole transport and hole injection, an electron blocking layer, a light-emitting layer, an electron transport layer, an electron injection layer, a layer that simultaneously performs electron transport and electron injection, and a hole blocking layer. It can be more than one floor. However, the structure of the organic light emitting device is not limited to this and may include fewer or more organic material layers.

In the organic light emitting device according to an exemplary embodiment of the present specification, the organic material layer includes one or more of a hole injection layer, a hole transport layer, an electron blocking layer, or a layer that simultaneously performs hole injection and transport.

In another embodiment, the organic layer may further include other organic compounds, metals, or metal compounds in addition to the compound represented by Formula 1 and the compound represented by Formula 2.

In the organic light-emitting device according to an exemplary embodiment of the present specification, the organic material layer includes a light-emitting layer.

In the organic light-emitting device according to an exemplary embodiment of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer includes a compound represented by Formula 1 and a compound represented by Formula 2.

In the organic light-emitting device according to an exemplary embodiment of the present specification, the light-emitting layer includes the compound represented by Formula 1 as a host of the light-emitting layer.

In the organic light-emitting device according to an exemplary embodiment of the present specification, the light-emitting layer includes two or more types of compounds represented by Formula 1 above as a host of the light-emitting layer.

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

In the organic light-emitting device according to an exemplary embodiment of the present specification, the light-emitting layer includes the compound represented by Formula 2 as a fluorescent dopant of the light-emitting layer.

In the organic light-emitting device according to an exemplary embodiment of the present specification, the light-emitting layer includes two or more compounds represented by Formula 2 as a dopant of the light-emitting layer.

In the organic light-emitting device according to an embodiment of the present specification, the light-emitting layer includes a compound represented by Formula 1 and Formula 2, and the compound represented by Formula 2 is 100 parts by weight of the compound represented by Formula 1. It is contained in an amount of 1 to 50 parts by weight, preferably in an amount of 1 to 20 parts by weight.

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 1 and the compound represented by Formula 2.

In the organic light emitting device according to an exemplary embodiment of the present specification, the light emitting layer further includes a fluorescent dopant or a phosphorescent dopant. At this time, the dopant in the light emitting layer is included in an amount of 1 to 50 parts by weight based on 100 parts by weight of the host.

According to an exemplary embodiment of the present specification, the organic light emitting device further includes one or more light emitting layers. At this time, the two or more light-emitting layers may be provided in contact with each other, or may be provided with an additional organic material layer between each light-emitting layer.

According to an exemplary embodiment of the present specification, the organic light-emitting device further includes one or more light-emitting layers, and the two or more light-emitting layers each have different wavelengths in which the maximum emission peak appears. That is, the wavelength band in which the maximum emission peak of the light-emitting layer containing the compound represented by Formula 1 and the compound represented by Formula 2 appears is different from the wavelength band in which the maximum emission peak of the added light-emitting layer appears.

According to an exemplary embodiment of the present specification, the organic light emitting device further includes one or more light emitting layers, and the two or more light emitting layers further include a fluorescent dopant or a phosphorescent dopant. At this time, the dopant in the light emitting layer is included in an amount of 1 to 50 parts by weight based on 100 parts by weight of the host.

According to an exemplary embodiment of the present specification, the organic light emitting device further includes one or more light emitting layers, and the two or more light emitting layers further include a fluorescent dopant or a phosphorescent dopant.

According to an exemplary embodiment of the present specification, the organic light-emitting device further includes one or more light-emitting layers, and among the two or more light-emitting layers, the light-emitting layer containing Formula 1 and Formula 2 uses the compound represented by Formula 1 as a host. , and includes the compound represented by Formula 2 as a fluorescent dopant.

According to an exemplary embodiment of the present specification, the organic light-emitting device further includes one or more light-emitting layers, and among the two or more light-emitting layers, in addition to the light-emitting layer containing the compound represented by Formula 1 and the compound represented by Formula 2, The light emitting layer included includes a phosphorescent dopant.

In this specification, the phosphorescent dopant and fluorescent dopant may be dopants commonly used in the art.

According to an exemplary embodiment of the present specification, the organic light emitting device further includes one or more light emitting layers, and the two or more light emitting layers are provided vertically or horizontally.

According to an exemplary embodiment of the present specification, the organic light emitting device further includes one or more light emitting layers, and the two or more light emitting layers are provided vertically.

According to an exemplary embodiment of the present specification, the organic light emitting device further includes one or more light emitting layers, and the two or more light emitting layers are provided horizontally.

According to an exemplary embodiment of the present specification, the organic light emitting device may further include two or more light emitting layers. At this time, the three or more light-emitting layers may be provided in contact with each other, or may be provided with an additional organic material layer between each light-emitting layer.

According to an exemplary embodiment of the present specification, the organic light-emitting device further includes two or more vertically arranged light-emitting layers, and the three or more light-emitting layers are blue fluorescent light-emitting layers.

In the organic light emitting device according to an exemplary embodiment of the present specification, the maximum emission peak (λ _max ) of the light emitting layer is 400 nm to 470 nm.

The organic light-emitting device according to an exemplary embodiment of the present specification includes two or more light-emitting layers, and the maximum emission peaks of the two or more light-emitting layers are respectively 400 nm to 500 nm, and preferably 400 nm to 470 nm.

The organic light-emitting device according to an embodiment of the present specification includes three or more layers of light-emitting layers, the maximum emission peak of one light-emitting layer (light-emitting layer 1) is 400 nm to 500 nm, and the peak of the light-emitting layer of another layer (light-emitting layer 2) is 400 nm to 500 nm. Maximum emission peak is 510 nm to 580 nm; Alternatively, it may exhibit a maximum emission peak of 610 nm to 680 nm, and the maximum emission peak of another layer of the light-emitting layer (emission layer 3) may have a maximum emission peak of 400 nm to 500 nm. At this time, the light-emitting layer 1 is a light-emitting layer containing a compound represented by the above-mentioned Chemical Formula 1 and the above-mentioned Chemical Formula 2.

According to an exemplary embodiment of the present specification, the organic material layer includes a hole injection layer, a hole transport layer, or an electron blocking layer, and the hole injection layer, a hole transport layer, or an electron blocking layer includes a compound represented by Formula 1.

According to an exemplary embodiment of the present specification, the organic material layer includes a hole blocking layer, an electron transport layer, an electron injection layer, or an electron injection and transport layer, and the hole blocking layer, the electron transport layer, the electron injection layer, and the transport layer are represented by the formula 1 Includes compounds that are

According to an exemplary embodiment of the present specification, the electron transport layer, electron injection layer, or electron injection and transport layer containing the compound represented by Formula 1 may further include an n-type dopant. As the n-type dopant, those known in the art can be used, for example, an alkali metal, an alkaline earth metal, an alkali metal compound, an alkaline earth metal compound, an alkali metal complex, or an alkaline earth metal complex. The metal compound may include an oxide or halide, and the complex may further include an organic ligand. For example, LiQ, etc. can be used. The n-type dopant may be included in an amount of 1% to 75% by weight, preferably 30% to 55% by weight, in the electron transport layer, electron injection layer, or electron injection and transport layer.

According to an exemplary embodiment of the present specification, the organic material layer is one layer among a hole transport layer, a hole injection layer, a hole transport and injection layer, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron transport and injection layer, and a hole blocking layer. It may include more than the above.

An organic light-emitting device according to an embodiment of the present specification includes one or more light-emitting layers, and one or more organic material layers are additionally provided between the two or more light-emitting layers, and the organic material layers include a hole transport layer, a hole injection layer, a hole transport and It may further include one or more of an injection layer, an electron blocking layer, a charge generation layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron transport and injection layer, and a hole blocking layer.

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.

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 specification 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 a substrate 1, an anode 2, a hole transport layer 4, a light-emitting layer 6, an electron injection and transport layer 8, and a cathode 11 are sequentially stacked. . In this structure, the compound represented by Formula 1 and the compound represented by Formula 2 may be included in the hole transport layer 4, the light-emitting layer 6, and the electron injection and transport layer 8.

In Figure 2, a substrate 1, an anode 2, a hole transport layer 4, a first emitting layer 6a, a second emitting layer 6b, an electron injection and transport layer 8, and a cathode 11 are sequentially stacked. The structure of an organic light emitting device is illustrated. In this structure, the compound represented by Formula 1 and the compound represented by Formula 2 are added to the hole transport layer 4, the first emitting layer 6a, the second emitting layer 6b, and the electron injection and transport layer 8. may be included.

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), an electron injection and transport layer (8), and a cathode (11). The structure of this sequentially stacked organic light emitting device is illustrated. In this structure, the compound represented by Formula 1 and the compound represented by Formula 2 are a hole injection layer (3), a hole transport layer (4), an electron blocking layer (5), a light emitting layer (6), an electron injection layer and It may be included in the transport layer (8).

According to an exemplary embodiment of the present specification, the organic light emitting device may have a tandem structure in which two or more independent devices are connected in series. In one embodiment, the tandem structure may be in a form in which each organic light-emitting device is bonded to a charge generation layer. Tandem-structured devices can be driven at lower currents than unit devices based on the same brightness, which has the advantage of greatly improving the device's lifespan characteristics.

According to an exemplary embodiment of the present specification, the organic material layer includes a first stack including one or more light-emitting layers; a second stack including one or more light emitting layers; and one or more hole transport layers, light emitting layers, or electron transport layers provided between the first stack and the second stack.

According to another embodiment of the present specification, the organic material layer includes a first stack including one or more light-emitting layers; a second stack including one or more light emitting layers; and a third stack including one or more light emitting layers, between the first stack and the second stack; and one or more hole transport layers, a light emitting layer, or an electron transport layer between the second stack and the third stack, respectively.

The first stack, the second stack, and the third stack each include one or more light emitting layers, and additionally include a hole injection layer, a hole transport layer, an electron blocking layer, an electron injection layer, an electron transport layer, a hole blocking layer, a hole transport layer, and a hole transport layer. It may further include one or more layers among a layer that performs simultaneous injection (hole injection and transport layer) and a layer that simultaneously performs electron transport and electron injection (electron injection and transport layer).

An organic light emitting device including the first stack and the second stack is illustrated in FIG. 4 .

4 shows a substrate 1, an anode 2, a hole injection layer 3, a first hole transport layer 4a, an electron blocking layer 5, a first light emitting layer 6a, a first electron transport layer 9a, An N-type charge generation layer (12), a P-type charge generation layer (13), a second hole transport layer (4b), a second light-emitting layer (6b), an electron injection and transport layer (8), and a cathode (11) are sequentially stacked. The structure of an organic light emitting device is illustrated. In this structure, the compound represented by Formula 1 may be included in the first hole transport layer (4a) or the second hole transport layer (4b), and the compound represented by Formula 2 may be included in the first emitting layer (6a) or the second hole transport layer (4b). 2 may be included in the light emitting layer 6b.

An organic light emitting device including the first to third stacks is illustrated in FIG. 5 .

5 shows a substrate 1, an anode 2, a hole injection layer 3, a first hole transport layer 4a, an electron blocking layer 5, a first light emitting layer 6a, a first electron transport layer 9a, First N-type charge generation layer (12a), first P-type charge generation layer (13a), second hole transport layer (4b), second light-emitting layer (6b), second electron transport layer (9b), second N-type charge An organic layer in which a generation layer (12b), a second P-type charge generation layer (13b), a third hole transport layer (4c), a third light emitting layer (6c), a third electron transport layer (9c), and a cathode (11) are sequentially stacked. The structure of the light emitting device is illustrated. In this structure, the compound represented by Formula 1 may be included in one or more layers among the first hole transport layer 4a, the second hole transport layer 4b, and the third hole transport layer 4c, and the compound represented by Formula 2 The compound represented by may be included in the first light-emitting layer 6a, the second light-emitting layer 6b, and the third light-emitting layer 6c.

The N-type charge generation layer is 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4TCNQ), fluorine-substituted 3,4,9,10-phene Rylenetetracarboxylic dianhydride (PTCDA), cyano-substituted PTCDA, naphthalenetetracarboxylic dianhydride (NTCDA), fluorine-substituted NTCDA, cyano-substituted NTCDA, hexaazatriphenyline derivatives It may be, but is not limited to this. In one embodiment, the N-type charge generation layer may simultaneously include a benzoimidazophenanthrinine-based derivative and a Li metal.

The P-type charge generation layer may simultaneously include an arylamine-based derivative and a compound containing a cyano group.

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, but are not limited to, multi-layered materials such as LiF/Al or LiO ₂ /Al.

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.

<Synthesis example>

Manufacturing Example 1

Compound A (19.80g, 51.69mmol) and naphthalene-2-ylboronic acid (8.89g, 51.69mmol) were completely dissolved in 300ml of tetrahydrofuran in a 500ml round-bottom flask under a nitrogen atmosphere, and then added to 2M potassium carbonate aqueous solution (150ml). After adding tetrakis-(triphenylphosphine)palladium (1.79 g, 1.55 mmol), it was heated and stirred for 3 hours. The temperature was lowered to room temperature (23 ± 5°C), the water layer was removed, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 180ml of ethyl acetate to prepare Compound C1 (13g, 59%). Additionally, HOST-1 was prepared by deuterium substitution in the same manner as in Scheme 3 described above.

MS[M+H] ⁺ = 448 ~ 452

Production example 2

Compound C2 was prepared in the same manner as Preparation Example 1, except that 4-naphthalen-2-ylphenylboronic acid was used instead of naphthalen-2-ylboronic acid. Additionally, HOST-2 was prepared by deuterium substitution in the same manner as in Scheme 3 described above.

MS[M+H]+= 516 ~ 532

Production example 3

Compound C3 was prepared in the same manner as Preparation Example 1, except that B was used instead of A in Preparation Example 1. Additionally, HOST-3 was prepared by deuterium substitution in the same manner as in Scheme 3 described above.

MS[M+H]+= 388 ~ 400

Production example 4

Compound 4 was prepared in the same manner as Preparation Example 1, except that C was used instead of A in Preparation Example 1. Additionally, HOST-4 was prepared by deuterium substitution in the same manner as in Scheme 3 described above.

MS[M+H]+= 465 ~ 480

Production example 5

Compound D (20g, 47.39mmol) and phenylboronic acid (5.78g, 47.39mmol) were completely dissolved in 300ml of tetrahydrofuran in a 500ml round bottom flask under a nitrogen atmosphere, then 2M potassium carbonate aqueous solution (150ml) was added, and Tetrakis -(Triphenylphosphine)palladium (1.79 g, 1.55 mmol) was added, and then heated and stirred for 3 hours. The temperature was lowered to room temperature (23 ± 5°C), the water layer was removed, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 180ml of ethyl acetate to prepare Compound C5 (11g, 58%). Additionally, HOST-5 was prepared by deuterium substitution in the same manner as in Scheme 3 described above.

MS[M+H] ⁺ = 428 ~ 440

Production example 6

Dissolve phenylbromide (1 eq) in tetrahydrofuran (THF) under a nitrogen atmosphere, and then slowly add n-BuLi (1.1 eq) dropwise at -78°C. After 30 minutes, 2-naphthalen-1-yl-anthracene-9,10-dione (1 eq) is added. When the reaction is completed after raising the temperature to room temperature, it is extracted with ethyl acetate and washed with water. Proceed with this method one more time using phenylbromide. After completion of the reaction, extraction was performed with ethyl acetate and washed with water. The intermediate can be obtained by evaporating all of the ethyl acetate and dropping the solid using hexane. Intermediate (1 eq), KI (3 eq), and NaPO ₂ H ₂ (5 eq) were added to acetic acid, the temperature was raised, and refluxed. After completion of the reaction, excess water is poured and the resulting solid is filtered. After extraction with ethyl acetate, washing with water, and recrystallization with toluene, compound C6 can be obtained with a yield of 70%. Additionally, HOST-6 was prepared by deuterium substitution in the same manner as in Scheme 3 described above.

MS[M+H] ⁺ =466 ~ 480

Production example 7

Dissolve 1-bromonaphthalene (1 eq) in tetrahydrofuran (THF) under a nitrogen atmosphere, and then slowly add n-BuLi (1.1 eq) dropwise at -78°C. After 30 minutes, add 2-(naphthalene-1-yl)anthracene-9,10-dione (1 eq). When the reaction is completed after raising the temperature to room temperature, it is extracted with ethyl acetate and washed with water. Proceed with this method one more time using 1-bromonaphthalene. After completion of the reaction, extraction was performed with ethyl acetate and washed with water. The intermediate can be obtained by evaporating all of the ethyl acetate and dropping the solid using hexane. Intermediate (1 eq), KI (3 eq), and NaPO ₂ H ₂ (5 eq) were added to acetic acid, the temperature was raised, and refluxed. After completion of the reaction, excess water is poured and the resulting solid is filtered. After extraction with ethyl acetate, washing with water, and recrystallization with toluene, compound C7 can be obtained with a yield of 70%. Additionally, HOST-7 was prepared by deuterium substitution in the same manner as in Scheme 3 described above.

MS[M+H] ⁺ =567 ~ 584

Production example 8

Dissolve phenylbromide (1 eq) in tetrahydrofuran (THF) under a nitrogen atmosphere, and then slowly add n-BuLi (1.1 eq) dropwise at -78°C. After 30 minutes, add 2-phenylanthracene-9,10-dione (1 eq). When the reaction is completed after raising the temperature to room temperature, it is extracted with ethyl acetate and washed with water. Proceed with this method one more time using phenylbromide. After completion of the reaction, extraction was performed with ethyl acetate and washed with water. The intermediate can be obtained by evaporating all of the ethyl acetate and dropping the solid using hexane. Intermediate (1 eq), KI (3 eq), and NaPO ₂ H ₂ (5 eq) were added to acetic acid, the temperature was raised, and refluxed. After completion of the reaction, excess water is poured and the resulting solid is filtered. After extraction with ethyl acetate, washing with water, and recrystallization with toluene, compound C8 can be obtained with a yield of 70%. Additionally, HOST-8 was prepared by deuterium substitution in the same manner as in Scheme 3 described above.

MS[M+H] ⁺ =415 ~ 428

Production example 9

Dissolve phenylbromide (1 eq) in tetrahydrofuran (THF) under a nitrogen atmosphere, and then slowly add n-BuLi (1.1 eq) dropwise at -78°C. After 30 minutes, 2-(dibenzo[b,d]furan-2-yl)anthracene-9,10-dione) Add (1 eq). When the reaction is completed after raising the temperature to room temperature, it is extracted with ethyl acetate and washed with water. Proceed with this method one more time using phenylbromide. After completion of the reaction, extraction was performed with ethyl acetate and washed with water. The intermediate can be obtained by evaporating all of the ethyl acetate and dropping the solid using hexane. Intermediate (1 eq), KI (3 eq), and NaPO ₂ H ₂ (5 eq) were added to acetic acid, the temperature was raised, and refluxed. After completion of the reaction, excess water is poured and the resulting solid is filtered. After extraction with ethyl acetate, washing with water, and recrystallization with toluene, compound C9 can be obtained with a yield of 70%. Additionally, HOST-9 was prepared by deuterium substitution in the same manner as in Scheme 3 described above.

MS[M+H] ⁺ =506 ~ 520

<Example 1-1>

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 from Fischer Co. was used, and distilled water filtered secondarily using a filter from 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, hexanitrile hexaazatriphenylene (HAT) of the formula below was thermally vacuum deposited to a thickness of 500 Å to form a hole injection layer.

A hole transport layer was formed by vacuum deposition (300 Å) of the following compound [HT 1], a hole transport material, on the hole injection layer.

Next, the following [HT 2] was vacuum deposited to a film thickness of 50 Å on the hole transport layer to form an electron blocking layer.

Next, HOST 1 and BD 1 as shown below were vacuum deposited on the electron blocking layer with a film thickness of 300 Å at a weight ratio of 25:1 to form a light emitting layer.

On the light emitting layer, the following ETL and LiQ (Lithium Quinolate) were vacuum deposited at a weight ratio of 1:1 to form an electron injection and transport layer with a thickness of 300 Å. A cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 12 Å and aluminum to a thickness of 2,000 Å on the electron injection and transport layer.

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 the deposition rate of aluminum was maintained at 2Å/sec, and the vacuum degree during deposition was 2 x 10 ^-7 . An organic light emitting device was manufactured by maintaining ~5 x 10 ^-6 torr.

<Examples 1-2 to 1-9>

An organic light-emitting device was manufactured in the same manner as Example 1-1, except that the compounds listed in Table 1 below were used instead of HOST 1 in Example 1-1.

<Comparative Examples 1-1 to 1-5>

An organic light-emitting device was manufactured in the same manner as Example 1-1, except that compounds C1 to C5 of the following structures were used instead of HOST 1 in Example 1-1.

<Comparative Examples 1-6 to 1-10>

In Example 1-1, HOSTs 1 to 5 were used, and an organic light emitting device was manufactured in the same manner as Example 1-1, except that BD 2 below was used instead of BD 1.

The driving voltage and luminous efficiency of the organic light emitting device were measured at a current density of 10 mA/cm ² , and the time (T ₉₀ ) for reaching 90% of the initial luminance was measured at a current density of 20 mA/cm ² . The results are shown in Table 1 below.

compound compound Voltage
(V@10mA/cm ² ) efficiency
(cd/A@10mA/cm ² ) Lifespan (h)
T ₉₀ at 20mA/cm ² Example 1-1 HOST 1 BD 1 4.47 5.72 173 Example 1-2 HOST 2 BD 1 4.47 5.71 178 Example 1-3 HOST 3 BD 1 4.49 5.73 154 Example 1-4 HOST 4 BD 1 4.51 5.72 174 Examples 1-5 HOST 5 BD 1 4.52 5.75 169 Example 1-6 HOST 6 BD 1 4.55 5.72 159 Example 1-7 HOST 7 BD 1 4.54 5.71 161 Examples 1-8 HOST 8 BD 1 4.58 5.66 166 Example 1-9 HOST 9 BD 1 4.61 5.67 171 Comparative Example 1-1 Compound C1 BD 1 4.94 5.52 101 Comparative Example 1-2 Compound C2 BD 1 4.83 5.53 112 Comparative Example 1-3 Compound C3 BD 1 4.82 5.52 104 Comparative Example 1-4 Compound C4 BD 1 4.91 5.53 109 Comparative Example 1-5 Compound C5 BD 1 4.90 5.55 110 Comparative Example 1-6 HOST 1 BD 2 4.71 4.94 175 Comparative Example 1-7 HOST 2 BD 2 4.72 5.02 178 Comparative Example 1-8 HOST 3 BD 2 4.74 4.89 158 Comparative Example 1-9 HOST 4 BD 2 4.79 4.88 180 Comparative Example 1-10 HOST 5 BD 2 4.80 5.01 167

From the results in Table 1, the organic light-emitting device using the deuterium-substituted hosts represented by HOST 1 to 9 simultaneously with BD 1 was Comparative Examples 1-1 to 1-5 using compounds C1 to C5 that were not substituted with deuterium as hosts. It can be seen that it exhibits excellent characteristics in terms of driving voltage, efficiency, and lifespan. This result shows that when the compound of Formula 1 and the compound of Formula 2 are used together, Forster-energy transfer, in which energy is transferred from the host represented by Formula 1 to the dopant, is maintained, and the deuterium This is because there is an effect of improving lifespan due to enthalpy stability.

In addition, it was confirmed that Examples 1-1 to 1-5 using BD 1 as a dopant showed increased efficiency and improved voltage while maintaining lifespan compared to Comparative Examples 1-6 to 1-10 using BD 2 as a dopant. You can.

1: substrate
2: anode
3: Hole injection layer
4: Hole transport layer
4a: first hole transport layer
4b: second hole transport layer
4c: Third hole transport layer
5: Electronic blocking layer
6: Light-emitting layer
6a: first light emitting layer
6b: second light emitting layer
6c: third light emitting layer
7: Hole blocking layer
8: Electron injection and transport layer
9a: first electron transport layer
9b: second electron transport layer
9c: Third electron transport layer
11: cathode
12: N-type charge generation layer
12a: First N-type charge generation layer
12b: Second N-type charge generation layer
13: P-type charge generation layer
13a: First P-type charge generation layer
13b: Second P-type charge generation layer

Claims (19)

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

In Formula 1,
Ar1 and Ar2 are the same or different from each other, and are each independently an aryl group substituted or unsubstituted with deuterium; Or a heterocyclic group substituted or unsubstituted with deuterium,
Ar3 is an aryl group unsubstituted or substituted with deuterium; Or a heterocyclic group substituted or unsubstituted with deuterium,
L1 to L3 are the same or different from each other and are each independently directly bonded; Arylene group substituted or unsubstituted with deuterium; or a divalent heterocyclic group substituted or unsubstituted with deuterium,
R1 is hydrogen; or deuterium,
a to c are integers from 0 to 3, and when a to c is 2 or more, the substituents in parentheses are the same or different from each other,
r1 is an integer from 0 to 7, and when r1 is 2 or more, R1 is the same as or different from each other,
The compound represented by Formula 1 is more than 80% substituted with deuterium,
[Formula 2]

In Formula 2,
A is a benzene ring,
B and C are two or more aromatic hydrocarbon rings; Or it is a heterocycle of two or more rings. delete The organic light emitting device according to claim 1, wherein the light emitting layer includes the compound represented by Formula 1 as a host of the light emitting layer. The organic light emitting device according to claim 1, wherein the light emitting layer includes the compound represented by Formula 2 as a dopant of the light emitting layer. The organic light-emitting device of claim 3, wherein the host includes two or more compounds represented by Formula 1. The organic light-emitting device according to claim 1, wherein the maximum emission peak (λ _max ) of the light-emitting layer is 400 nm to 470 nm. delete In claim 1,
An organic light-emitting device wherein at least one of B and C is represented by any one of the following formulas 3 to 7:
[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

In Formulas 3 to 7, * refers to the condensation position,
X is O; or S,
G1 and G11 are each independently hydrogen,
g1 and g11 are each 6. In claim 1,
Formula 2 is an organic light-emitting device represented by the following Formula 2-1 or Formula 2-2:
[Formula 2-1]

[Formula 2-2]

In Formulas 2-1 and 2-2, the definition of A is the same as the definition in Formula 2,
X and Y are the same or different from each other and are each independently O; or S,
G1 to G4 are each independently hydrogen,
n is 0 to 2,
g1 and g2 are each independently 6,
g4 is 4,
g3 is 2. The organic light-emitting device according to claim 1, wherein the compound represented by Formula 1 is represented by one of the following compounds:

In the above structural formula, v, w, x, y and z mean the substitution rate (%) of deuterium (D) compared to the total hydrogen that can be substituted in the structural formula,
v+w+x+y+z is 80% to 100%. The organic light-emitting device according to claim 1, wherein the compound represented by Formula 2 is represented by one of the following compounds:


. In claim 3,
The organic light emitting device further includes one or more light emitting layers. In claim 12,
An organic light-emitting device in which the two or more light-emitting layers each have different wavelengths in which the maximum emission peak appears. In claim 12,
The light-emitting layer including the compound represented by Formula 1 and the compound represented by Formula 2 includes the compound represented by Formula 1 as a host and the compound represented by Formula 2 as a fluorescent dopant. device. In claim 14,
An organic light emitting device wherein, in addition to the light emitting layer containing the compound represented by Formula 1 and the compound represented by Formula 2, the light emitting layer further included includes a phosphorescent dopant. The organic light emitting device according to claim 12, wherein the two or more light emitting layers are provided vertically or horizontally. The organic light emitting device according to claim 1, wherein the organic light emitting device further includes two or more vertically arranged light emitting layers, and the three or more light emitting layers are blue fluorescent light emitting layers. In claim 1,
The organic material layer further includes one or more of a hole transport layer, a hole injection layer, a hole transport and injection layer, an electron blocking layer, an electron transport layer, an electron injection layer, an electron transport and injection layer, and a hole blocking layer. An organic light emitting device. In claim 17,
The organic light-emitting device is further provided with one or more organic material layers between the two or more light-emitting layers, and the organic material layer includes a hole transport layer, a hole injection layer, a hole transport and injection layer, an electron blocking layer, a charge generation layer, a light-emitting layer, and an electron transport layer. , an organic light emitting device further comprising one or more layers of an electron injection layer, an electron transport and injection layer, and a hole blocking layer.