KR102567282B1 - Organic light emitting device - Google Patents

Abstract

The present specification is a first electrode; a second electrode; and 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 It provides an organic light emitting device that is to do.

Description

Organic light emitting device {ORGANIC LIGHT EMITTING DEVICE}

The present specification relates to an organic light emitting device.

The organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from the two electrodes are combined in the organic thin film to form a pair, and then emit light while disappearing. 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 complex compounds in which organic materials and metals are complexed. can be distinguished. Here, as the hole injection material or the hole transport material, an organic material having a p-type property, that is, an organic material that is easily oxidized and has an electrochemically stable state when oxidized is mainly used. On the other hand, as an electron injection material or electron transport material, an organic material having an n-type property, that is, an organic material that is easily reduced and has an electrochemically stable state upon reduction is mainly used. As the material of the light emitting layer, a material having both p-type and n-type properties, that is, a material having a stable form in both oxidation and reduction states is preferable, and excitons generated by recombination of holes and electrons in the light emitting layer are formed. A material with high luminous efficiency that converts it into light when it is damaged is preferred.

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 the present specification, an organic light emitting device having long lifespan characteristics is provided.

An exemplary embodiment of the present specification

a first electrode;

a second electrode;

and an organic material layer provided between the first electrode and the second electrode,

The organic material layer includes a light emitting layer,

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

[Formula 1]

In Formula 1,

Ar1 to Ar3 are the same as or different from each other, and each independently deuterium; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

L1 to L3 are the same as or different from each other, and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,

R1 is hydrogen; heavy hydrogen; halogen group; nitrile group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted thioalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted aralkyl group; or 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 are 2 or more, the substituents in parentheses are the same as or different from each other,

r1 is an integer from 0 to 7, and when r1 is 2 or more, R1 are 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 as or different from each other, and each independently a substituted or unsubstituted aromatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic ring.

An organic light emitting device having a long lifespan can be obtained by simultaneously including the compound represented by Formula 1 and the compound represented by Formula 2 in the organic light emitting device of the present invention.

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

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

This specification

a first electrode;

a second electrode;

and an organic material layer provided between the first electrode and the second electrode,

The organic material layer includes a light emitting layer,

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

In Chemical Formula 1, hydrogen, deuterium, an aryl group, or a heterocyclic group are connected to carbons 1, 8, and 10 of anthracene. In addition, since Chemical Formula 1 contains at least one deuterium, the efficiency and lifetime of the device are improved. Specifically, when hydrogen is replaced by deuterium, the chemical properties of the compound hardly change. However, since the atomic weight of deuterium is twice that of hydrogen, deuterated compounds may change their physical properties. For example, a compound substituted with deuterium lowers the vibrational energy level. A compound substituted with deuterium can prevent a decrease in quantum efficiency due to a decrease in intermolecular van der Waals force or a collision due to intermolecular vibration. C-D bonds can also improve the stability of compounds. Accordingly, the compound represented by Formula 1 may improve the efficiency and lifetime of the device by including deuterium.

The compound represented by Chemical 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 using a deuterated compound as a precursor, or deuterium is introduced into the compound through a hydrogen-deuterium exchange reaction using a deuterated solvent under an acid catalyst. You may.

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

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

In the present specification, when a certain component is said to "include", it means that it may further include other components without excluding other components unless otherwise stated.

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 the present specification, the "layer" means compatible with 'film' mainly used in the art, and means a coating covering a target area. The size of the 'layer' is not limited, and the size of each 'layer' may be the same or different. In one embodiment, the size of a 'layer' may be the same as the size of an entire device, may correspond to the size of a specific functional region, or may be as small as a single sub-pixel.

In this specification, the meaning that a specific material A is included in the B layer means that i) one or more types of material A are included in one layer B, and ii) the layer B is composed of one or more layers, and the material A is a multi-layer B All of the layers included in one or more layers are included.

In the present specification, the meaning that a specific material A is included in the C layer or the D layer means that i) included in one or more of the one or more C layers, ii) included in one or more of the one or more D layers, or iii ) means all of those included in one or more C layers and one or more D layers, respectively.

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

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

In this specification, " " means the position to be bonded to the formula or compound.

Examples of substituents in the present 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 replaced with another substituent, and the position to be substituted is not limited as long as the hydrogen atom is substituted, that is, a position where the substituent is substituted, and when two or more are substituted , Two or more substituents may be the same as or different from each other.

In this specification, the term "substituted or unsubstituted" means deuterium; halogen group; nitrile group; nitro group; hydroxy group; carbonyl group; ester group; imide group; amino group; silyl group; boron group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; and a substituted or unsubstituted heterocyclic group, which is substituted with one or two or more substituents selected from the group consisting of two or more substituents among the substituents exemplified above, or a substituent in which two or more substituents are connected. For example, "a substituent in which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which two phenyl groups are connected.

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

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

In the present specification, the silyl group may be represented by a chemical formula of -SiY _a Y _b Y _c , wherein Y _a , Y _b and Y _c are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like, but is not limited thereto. don't

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

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

In the present specification, the alkoxy group may be straight chain, branched chain or cyclic chain. The number of carbon atoms in 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.

Alkyl groups, alkoxy groups, and substituents containing other alkyl moieties described herein include both straight-chain and branched forms.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 6. Specifically, there are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like, but are 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 number of carbon atoms of the aryl group is 6 to 30. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 20. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, etc. as a monocyclic aryl group, but is not limited thereto. The polycyclic aryl group may be 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 bonded to 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 thereto.

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

In the present specification, the heterocyclic group is a ring 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 preferably has 2 to 60 carbon atoms. According to one embodiment, the carbon number of the heterocyclic group is 2 to 30. Examples of the heterocyclic group include a pyridine group, a pyrrole group, a pyrimidine group, a quinoline group, a pyridazinyl group, a furan group, a thiophene group, an imidazole group, a pyrazole group, a dibenzofuran group, and a dibenzothiophene group. , A carbazole group, a benzocarbazole group, a naphthobenzofuran group, a benzonaphthothiophene group, and an indenocarbazole group, but are not limited thereto.

In the present specification, 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 bonding with adjacent groups, "ring" refers to a hydrocarbon ring; or a heterocyclic ring.

The hydrocarbon ring may be an aromatic, aliphatic, or 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 description of the aryl group may be applied except that the aromatic hydrocarbon ring is divalent.

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

An exemplary embodiment of the present specification is a first electrode; a second electrode; and 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 comprises a compound represented by Formula 1 and a compound represented by Formula 2 below. It provides an organic light emitting device comprising a.

[Formula 1]

In Formula 1,

Ar1 to Ar3 are the same as or different from each other, and each independently deuterium; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

L1 to L3 are the same as or different from each other, and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,

R1 is hydrogen; heavy hydrogen; halogen group; nitrile group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted thioalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted aralkyl group; or 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 are 2 or more, the substituents in parentheses are the same as or different from each other,

r1 is an integer from 0 to 7, and when r1 is 2 or more, R1 are 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 as or different from each other, and each independently a substituted or unsubstituted aromatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic ring.

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

In one embodiment of the present specification, the Ar1 to Ar3 are the same as or different from each other, and each independently deuterium; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, Ar1 to Ar3 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, Ar1 to Ar3 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

In one embodiment of the present specification, Ar1 to Ar3 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In one embodiment of the present specification, Ar1 to Ar3 are the same as or different from each other, and each independently represents a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted spirobifluorenyl group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted naphthobenzofuran group; A substituted or unsubstituted naphthobenzothiophene group; A substituted or unsubstituted indolocarbazole group; A substituted or unsubstituted xanthene group; A substituted or unsubstituted acridine group; Or a substituted or unsubstituted benzoimidazole group.

In one embodiment of the present specification, Ar1 to Ar3 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with one or more groups from the group consisting of deuterium, an alkyl group, and an aryl group or two or more connected groups; A biphenyl group unsubstituted or substituted with one or more groups or two or more linked groups from the group consisting of heavy hydrogen, an alkyl group, and an aryl group; a naphthyl group unsubstituted or substituted with one or more groups or two or more linked groups from the group consisting of heavy hydrogen, an alkyl group, and an aryl group; A fluorenyl group unsubstituted or substituted with one or more groups or two or more connected groups from the group consisting of heavy hydrogen, an alkyl group, and an aryl group; A spirobifluorenyl group unsubstituted or substituted with one or more groups or two or more linked groups from the group consisting of deuterium, an alkyl group, and an aryl group; A carbazole group unsubstituted or substituted with one or more groups or two or more linked groups from the group consisting of heavy hydrogen, an alkyl group, and an aryl group; A dibenzofuran group unsubstituted or substituted with one or more groups or two or more linked groups from the group consisting of deuterium, alkyl and aryl groups; a dibenzothiophene group unsubstituted or substituted with one or more groups or two or more linked groups from the group consisting of heavy hydrogen, an alkyl group, and an aryl group; A naphthobenzofuran group unsubstituted or substituted with one or more groups or two or more linked groups from the group consisting of heavy hydrogen, an alkyl group, and an aryl group; A naphthobenzothiophene group unsubstituted or substituted with one or more groups or two or more linked groups from the group consisting of deuterium, alkyl and aryl groups; an indolocarbazole group unsubstituted or substituted with one or more groups or two or more linked groups from the group consisting of heavy hydrogen, an alkyl group, and an aryl group; A xanthene group unsubstituted or substituted with one or more groups or two or more linked groups from the group consisting of deuterium, alkyl and aryl groups; an acridine group unsubstituted or substituted with one or more groups or two or more linked groups from the group consisting of deuterium, an alkyl group, and an aryl group; Or a benzoimidazole group unsubstituted or substituted with one or more groups or two or more groups from the group consisting of heavy hydrogen, an alkyl group, and an aryl group.

In an exemplary embodiment of the present specification, Ar1 to Ar3 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with one or more groups from the group consisting of deuterium, a methyl group, and a phenyl group, or two or more connected groups; A biphenyl group unsubstituted or substituted with one or more groups or two or more linked groups from the group consisting of deuterium, methyl and phenyl groups; a naphthyl group unsubstituted or substituted with one or more groups or two or more linked groups from the group consisting of deuterium, methyl and phenyl groups; A fluorenyl group unsubstituted or substituted with one or more groups or two or more linked groups from the group consisting of deuterium, methyl and phenyl groups; A spirobifluorenyl group unsubstituted or substituted with one or more groups or two or more linked groups from the group consisting of deuterium, methyl and phenyl groups; A carbazole group unsubstituted or substituted with one or more groups or two or more linked groups from the group consisting of deuterium, methyl and phenyl groups; a dibenzofuran group unsubstituted or substituted with one or more groups or two or more linked groups from the group consisting of deuterium, methyl and phenyl groups; A dibenzothiophene group unsubstituted or substituted with one or more groups or two or more linked groups from the group consisting of deuterium, methyl and phenyl groups; A naphthobenzofuran group unsubstituted or substituted with at least one group or two or more linked groups from the group consisting of deuterium, methyl group, and phenyl group; A naphthobenzothiophene group unsubstituted or substituted with one or more groups or two or more linked groups from the group consisting of deuterium, methyl and phenyl groups; an indolocarbazole group unsubstituted or substituted with one or more groups or two or more linked groups from the group consisting of deuterium, methyl and phenyl groups; a xanthene group unsubstituted or substituted with one or more groups or two or more linked groups from the group consisting of deuterium, methyl and phenyl groups; an acridine group unsubstituted or substituted with at least one group or two or more linked groups from the group consisting of deuterium, methyl group, and phenyl group; Or a benzoimidazole group unsubstituted or substituted with one or more groups or two or more groups from the group consisting of deuterium, methyl and phenyl groups.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with one or more groups or two or more linked groups from the group consisting of deuterium, a methyl group, and a phenyl group; A biphenyl group unsubstituted or substituted with one or more groups or two or more linked groups from the group consisting of deuterium, methyl and phenyl groups; a naphthyl group unsubstituted or substituted with one or more groups or two or more linked groups from the group consisting of deuterium, methyl and phenyl groups; Or a fluorenyl group unsubstituted or substituted with one or more groups or two or more linked groups from the group consisting of deuterium, methyl and phenyl groups.

In one embodiment of the present specification, Ar3 is a phenyl group unsubstituted or substituted with one or more groups or two or more groups from the group consisting of deuterium, methyl and phenyl groups; A biphenyl group unsubstituted or substituted with one or more groups or two or more linked groups from the group consisting of deuterium, methyl and phenyl groups; a naphthyl group unsubstituted or substituted with one or more groups or two or more linked groups from the group consisting of deuterium, methyl and phenyl groups; A fluorenyl group unsubstituted or substituted with one or more groups or two or more linked groups from the group consisting of deuterium, methyl and phenyl groups; A spirobifluorenyl group unsubstituted or substituted with one or more groups or two or more linked groups from the group consisting of deuterium, methyl and phenyl groups; A carbazole group unsubstituted or substituted with one or more groups or two or more linked groups from the group consisting of deuterium, methyl and phenyl groups; a dibenzofuran group unsubstituted or substituted with one or more groups or two or more linked groups from the group consisting of deuterium, methyl and phenyl groups; A dibenzothiophene group unsubstituted or substituted with one or more groups or two or more linked groups from the group consisting of deuterium, methyl and phenyl groups; A naphthobenzofuran group unsubstituted or substituted with at least one group or two or more linked groups from the group consisting of deuterium, methyl group, and phenyl group; A naphthobenzothiophene group unsubstituted or substituted with one or more groups or two or more linked groups from the group consisting of deuterium, methyl and phenyl groups; an indolocarbazole group unsubstituted or substituted with one or more groups or two or more linked groups from the group consisting of deuterium, methyl and phenyl groups; a xanthene group unsubstituted or substituted with one or more groups or two or more linked groups from the group consisting of deuterium, methyl and phenyl groups; an acridine group unsubstituted or substituted with at least one group or two or more linked groups from the group consisting of deuterium, methyl group, and phenyl group; Or a benzoimidazole group unsubstituted or substituted with one or more groups or two or more groups from the group consisting of deuterium, methyl and phenyl groups.

In one embodiment of the present specification, Ar1 and Ar2 are identical to each other, and Ar1, Ar2, and Ar3 are different from each other.

In one embodiment of the present specification, the L1 to L3 are the same as or different from each other, and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group.

In one embodiment of the present specification, the L1 to L3 are the same as or different from each other, and are each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted divalent heterocyclic group having 6 to 60 carbon atoms.

In one embodiment of the present specification, the L1 to L3 are the same as or different from each other, and are each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted divalent heterocyclic group having 6 to 30 carbon atoms.

In one embodiment of the present specification, the L1 to L3 are the same as or different from each other, and are each independently a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted acridine group; Or a substituted or unsubstituted benzoimidazole group.

In one embodiment of the present specification, the L1 to L3 are the same as or different from each other, and are each independently a direct bond; A phenylene group unsubstituted or substituted with heavy hydrogen; A naphthylene group unsubstituted or substituted with heavy hydrogen; A carbazole group unsubstituted or substituted with heavy hydrogen; Acridine group unsubstituted or substituted with heavy hydrogen; or a benzoimidazole group unsubstituted or substituted with deuterium.

In one embodiment of the present specification, R1 is hydrogen; heavy hydrogen; halogen group; nitrile group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted thioalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted aralkyl group; or 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 one 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 Chemical Formula 1 is substituted with deuterium by 30% or more. In another exemplary embodiment, the compound represented by Formula 1 is substituted by 40% or more of deuterium. In another exemplary embodiment, the compound represented by Formula 1 is substituted by 50% or more of deuterium. In another exemplary embodiment, the compound represented by Formula 1 is substituted with deuterium by 60% or more. In another exemplary embodiment, the compound represented by Formula 1 is 70% or more substituted with deuterium. In another exemplary embodiment, the compound represented by Formula 1 is 80% or more substituted with deuterium. In another exemplary embodiment, the compound represented by Formula 1 is 90% or more substituted 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, u, v, w, x, y, and z mean the substitution rate (%) of deuterium (D) relative to all hydrogen that can be substituted in the structural formula,

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

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

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

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

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

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

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

In one embodiment of the present specification, A to C are the same as or different from each other, and each independently a substituted or unsubstituted aromatic hydrocarbon ring; or a substituted or unsubstituted heterocyclic ring.

In one embodiment of the present specification, A to C are the same as or different from each other, and each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic ring having 2 to 60 carbon atoms.

In one embodiment of the present specification, A to C are the same as or different from each other, and each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic ring having 2 to 30 carbon atoms.

In one embodiment of the present specification, A to C are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic to 6-cyclic aromatic hydrocarbon ring; Or a substituted or unsubstituted monocyclic to 6-cyclic heterocyclic ring.

In one embodiment of the present specification, A to C are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic to 4-cyclic aromatic hydrocarbon ring; Or a substituted or unsubstituted monocyclic to 4-cyclic heterocyclic ring.

In one embodiment of the present specification, A to C are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic to tricyclic aromatic hydrocarbon ring; Or a substituted or unsubstituted monocyclic to tricyclic heterocyclic ring.

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

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

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

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

In one embodiment of the present specification, B and C are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic to 4-cyclic aromatic hydrocarbon ring; Or a substituted or unsubstituted monocyclic to tricyclic heterocyclic ring.

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

In one embodiment of the present specification, B and C are the same as 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 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 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 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; 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 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 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 a dibenzothiophene 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.

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

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

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

In an exemplary embodiment of the present specification, A is a bicyclic or more ring.

In an exemplary embodiment of the present specification, B is a bicyclic or more ring.

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

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 an exemplary embodiment of the present specification, B and C are two or more rings.

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

In one embodiment of the present specification, at least one of B and C is represented by any one of Formulas 3 to 7 below.

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

In Chemical Formulas 3 to 7, * means a condensed position,

X is NRa; O; S; or CRbRc;

Ra to Rc are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group, or bonded to an adjacent group to form a substituted or unsubstituted ring;

G1 and G11 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; nitrile group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; or 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 as or different from each other.

In one embodiment of the present specification, Formula 2 is represented by Formula 2-1 or Formula 2-2 below.

[Formula 2-1]

[Formula 2-2]

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

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

Ra to Rc are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group, or bonded to an adjacent group to form a substituted or unsubstituted ring;

G1 to G4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; nitrile group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; or 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 each independently represents an integer of 0 to 6, and when g1 and g2 are 2 or more, the substituents in parentheses are the same as or different from each other,

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

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

In one embodiment of the present specification, the Ra to Rc are the same as or different from each other, and 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 bonded to an adjacent group to form a substituted or unsubstituted ring having 6 to 30 carbon atoms.

In one embodiment of the present specification, the Ra to Rc are the same as or different from each other, and 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 bonded to an adjacent group to form a substituted or unsubstituted ring having 6 to 20 carbon atoms.

In one embodiment of the present specification, the Ra to Rc are the same as or different from each other, and each independently a methyl group; or a phenyl group, or bonded to an adjacent group to form a fluorene ring.

In one embodiment of the present specification, G1 to G4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms, or adjacent groups combine with each other to form a substituted or unsubstituted ring having 6 to 30 carbon atoms.

In one embodiment of the present specification, G1 to G4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 15 carbon atoms; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or adjacent groups combine with each other to form a substituted or unsubstituted ring having 6 to 15 carbon atoms.

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

In one embodiment of the present specification, G1 to G4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; It is an amine group unsubstituted or substituted with a phenyl group, or adjacent groups combine 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 one embodiment of the present specification, g1 and g2 are 1 or 2.

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

The definition of the substituent is as defined in Formula 2-1.

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

The definition of the substituent is as defined 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 Reaction Schemes 1 to 3 below, but is not limited thereto. In addition, the compounds prepared according to Reaction Schemes 1 and 2 may be substituted with deuterium through the same process as Reaction Scheme 3. At this time, in Scheme 3, the deuterium substitution rate is 40% to 100%. In Schemes 1 to 3 below, the type and number of substituents can be determined by appropriately selecting known starting materials by those skilled in the art. Reaction type and reaction conditions may be used those known in the art.

[Scheme 1]

[Scheme 2]

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

Hereinafter, the organic light emitting element will be described.

In one embodiment of the present specification, the organic material layer of the organic light emitting device further includes two or more compounds, and the compound represented by Formula 1 excluding the compound represented by Formula 2 and a triplet of the two or more 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 three of the two or more compounds is 2.7 eV or more. In this case, the compound represented by Formula 2 may act as a light emitting dopant, and the two or more compounds may have a Forster energy transfer efficiency of 90% or more to the light emitting dopant due to an energy barrier, but are limited thereto. it is not going to be

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 hole transport and hole injection layer, an electron blocking layer, and a light emitting layer. , an electron transport layer, an electron injection layer, a layer that simultaneously transports and injects electrons, or a hole blocking layer. That is, the two or more compounds are a hole injection layer, a hole transport layer, a layer that simultaneously transports and injects holes, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, a layer that simultaneously transports and injects electrons, or a hole blocking layer. It can be a compound included in the layer.

In the present specification, the triplet energy can be measured using a spectroscopic instrument capable of measuring fluorescence and phosphorescence, and in the case of measurement conditions, toluene or TF as a solvent in a cryogenic state using liquid nitrogen at a concentration of 10 ^-6 M A solution is prepared, the solution is irradiated with a light source in the absorption wavelength range of the material, and singlet emission is excluded from the emission spectrum, and the triplet emission spectrum is analyzed and confirmed. When the electrons are reversed from the light source, the time for the electrons to stay in the triplet is much longer than the time they stay in the singlet, so the separation of the two components is possible in a cryogenic state.

The organic light emitting device of the present invention can be manufactured by a conventional organic light emitting device manufacturing method and materials, except for forming an organic material layer using the compound represented by the above formula (1) and the compound represented by the above formula (2). 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 as 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 coating method means 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 including only the organic material layer, but may have a structure further including additional organic material layers. As the additional organic material layer, one of a hole injection layer, a hole transport layer, a layer that simultaneously transports and injects holes, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, a layer that simultaneously transports and injects electrons, and a hole blocking layer It can be more than one layer. However, the structure of the organic light emitting device is not limited thereto 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 at least one of a hole injection layer, a hole transport layer, an electron blocking layer, or a hole injection and transport layer.

In another exemplary embodiment, the organic material layer may further include other organic compounds, metals, or metal compounds in addition to the compound represented by Chemical Formula 1 and the compound represented by Chemical 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 Chemical Formula 1 and a compound represented by Chemical 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 Chemical 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 kinds of compounds represented by Chemical 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 the compound represented by Chemical 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 Chemical 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 kinds of compounds represented by Chemical Formula 2 as dopants 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 compounds 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 1 part by weight to 50 parts by weight, preferably 1 part by weight to 20 parts by weight.

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

In the organic light emitting device according to one 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 1 part by weight 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. In this case, the two or more light emitting layers may be provided in contact with each other, or may be provided by including an additional organic material layer between each light emitting layer.

According to one 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 have different wavelength bands in which the maximum emission peak appears. That is, the wavelength band in which the emission peak of the emission layer including the compound represented by Formula 1 and the compound represented by Chemical Formula 2 appears is different from the wavelength band in which the maximum emission peak appears in the added emission layer.

According to one 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 1 part by weight to 50 parts by weight based on 100 parts by weight of the host.

According to one 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 including Formula 1 and Formula 2 uses the compound represented by Formula 1 as a host. , The compound represented by Formula 2 is included 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 in addition to the light emitting layer including the compound represented by Formula 1 and the compound represented by Formula 2 among the two or more light emitting layers, an additional light emitting layer is added. The light emitting layer included as includes a phosphorescent dopant.

In the present specification, dopants commonly used in the art may be used as the phosphorescent dopant and the 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 the two or more light emitting layers are provided vertically or horizontally.

According to one 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 one 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 one embodiment of the present specification, the organic light emitting device may further include two or more light emitting layers. In this case, the three or more light emitting layers may be provided in contact with each other, or may be provided by including an additional organic material layer between each light emitting layer.

According to one embodiment of the present specification, the organic light emitting device further includes two or more light emitting layers provided vertically, 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 emission layer is 400 nm to 470 nm.

An organic light emitting device according to an exemplary embodiment of the present specification includes two or more light emitting layers, and each of the two or more light emitting layers has a maximum emission peak of 400 nm to 500 nm, preferably 400 nm to 470 nm.

An organic light emitting device according to an exemplary embodiment of the present specification includes three or more light emitting layers, the maximum emission peak of one light emitting layer (light emitting layer 1) is 400 nm to 500 nm, and the light emitting layer of another layer (light emitting layer 2) The maximum emission peak is between 510 nm and 580 nm; Alternatively, a maximum emission peak of 610 nm and 680 nm may be exhibited, and a maximum emission peak of another light emitting layer (emitting layer 3) may exhibit a maximum emission peak of 400 nm to 500 nm. In this case, the light emitting layer 1 is a light emitting layer including the 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, the hole transport layer, or the electron blocking layer includes the 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, electron transport layer, electron injection layer, and transport layer are represented by Chemical Formula 1 contains a compound that is

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

According to one embodiment of the present specification, the organic material layer is one layer of 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. More may be included.

An organic light emitting device according to an exemplary embodiment of the present specification includes one or more light emitting layers, and one or more organic material layers are further 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 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 may be further included.

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 organic light emitting device of an inverted type 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 a structure as shown in FIGS. 1 to 3 , but is not limited thereto.

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.

2, a substrate 1, an anode 2, a hole transport layer 4, a first light emitting layer 6a, a second light emitting layer (b), an electron injection and transport layer 8, and a cathode 11 are sequentially stacked. The structure of the organic light emitting element is exemplified. In this structure, the compound represented by Formula 1 and the compound represented by Formula 2 are applied to the hole transport layer 4, the first light emitting layer 6a, the second light emitting layer (b), and the electron injection and transport layer 8. can 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 element is illustrated. In such a 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, electron injection and It may be included in the transport layer (8).

According to one 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 a form in which each organic light emitting device is bonded to a charge generation layer. Since the element of the tandem structure can be driven at a lower current than the unit element based on the same brightness, there is an advantage in that the lifetime characteristics of the element are greatly improved.

According to one embodiment of the present specification, the organic material layer may include 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 exemplary embodiment of the present specification, the organic material layer may include 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, wherein the first stack is disposed between the second stack; and one or more hole transport layers, light emitting layers, or electron transport layers 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 further 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 of a layer that performs simultaneous injection (hole injection and transport layer) and a layer that simultaneously transports and injects electrons (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 the organic light emitting element is exemplified. In such a 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 light 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 element 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-phenol Lylenetetracarboxylic dianhydride (PTCDA), cyano-substituted PTCDA, naphthalenetetracarboxylic dianhydride (NTCDA), fluorine-substituted NTCDA, cyano-substituted NTCDA, hexaazatriphenyline derivatives etc., but is not limited thereto. In an exemplary embodiment, the N-type charge generation layer may simultaneously include a benzoimidazophenanthrinine-based derivative and 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 uses a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to form a metal or conductive metal oxide or an alloy thereof on a substrate. deposited to form an anode, form 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 deposit a material that can be used as a cathode thereon. It can be. In addition to this method, an organic light emitting device may be fabricated by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

One or more layers of organic material are provided between the first electrode and the second electrode, and the organic material 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 at least one layer of hole transport and injection layers.

The organic material layer may have a multilayer structure including a hole injection layer, a hole transport layer, an electron injection and electron transport layer, an electron blocking layer, a light emitting layer and an electron transport layer, an electron injection layer, and an electron transport and injection layer, but is limited thereto. It may be a single-layer structure. In addition, the organic material layer can be formed by a solvent process other than a deposition method using various polymer materials, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or a thermal transfer method. Can be made in layers.

The anode is an electrode for injecting holes, and a material having a high work function is preferable so that holes can be smoothly injected into the organic material layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides 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, but are not limited thereto.

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

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 molecular orbital) is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrilehexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene-based organic materials. of organic materials, anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited thereto. The hole injection layer may have a thickness of 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 characteristic from deteriorating, and if it is 150 nm or less, the thickness of the hole injection layer is too thick to increase the driving voltage to improve the movement of holes. There are advantages to avoiding this.

The hole transport layer may play a role of facilitating hole transport. As the hole transport material, a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer, and a material having high hole mobility is suitable. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated parts.

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

An electron blocking layer may be provided between the hole transport layer and the light emitting layer. For the electron blocking layer, the aforementioned compounds or materials known in the art may be used.

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 ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; Polyfluorene, rubrene, etc., but are not limited thereto.

A host material for the light emitting layer includes a condensed aromatic ring derivative or a compound containing a hetero ring. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type furan compounds, pyrimidine derivatives, etc., but are not limited thereto.

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

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 serve to facilitate electron transport. As the electron transport material, a material capable of receiving electrons well from the cathode and transferring them to the light emitting layer, and a material having high electron mobility is suitable. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes containing Alq ₃ ; organic radical compounds; hydroxyflavone-metal complexes and the like, but are not limited thereto. The thickness of the electron transport layer may be 1 to 50 nm. If the thickness of the electron transport layer is 1 nm or more, there is an advantage in preventing deterioration of electron transport properties, and if it is 50 nm or less, the thickness of the electron transport layer is too thick to prevent an increase in driving voltage to improve electron movement. There are advantages that can be

The electron injection layer may serve to smoothly inject electrons. The electron injecting material has the ability to transport electrons, has an excellent electron injecting 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 , compounds having excellent thin film forming ability are preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preonylidene methane, anthrone, etc. and their derivatives, metals complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

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

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

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

Hereinafter, examples will be described in detail in order to specifically describe the present specification. However, the embodiments according to the present specification may be modified in many different forms, and the scope of the present application is not construed as being limited to the embodiments detailed below. The embodiments of the present application are provided to more completely explain the present specification to those skilled in the art.

<Synthesis example>

Preparation Example 1: Preparation of Compound A

1,8-dichloroanthraquinone (50 g, 180 mmol) was dissolved in aqueous ammonia (2000 L), and Zn dust (1500 g) was added and stirred under reflux. After the reaction was completed, it was cooled to room temperature, filtered, and the organic layer was separated from the reaction filtrate. The organic layer was dried with magnesium sulfate, distilled under reduced pressure, recrystallized with hexane, and the solid obtained was dissolved in isopropyl alcohol, concentrated hydrochloric acid was added, and stirred under reflux for 5 hours. let it After the reaction was completed, it was cooled to room temperature, and the resulting solid was filtered, washed with water, and dried to obtain Compound A (27.8 g, 63%).

MS [M ⁺ ] = found 246.33, calc. 246.00

Preparation Example 2: Preparation of Compound B

Compound A (20g, 80.9 mmol), 1-bromonaphthaleneboronic acid (30.6 g, 178 mmol), Pd(dba) ₂ (1.40 g, 2.43 mmol), PCy ₃ (1.36 g, 4.86 mmol) was added to 2M K ₃ It was added to PO ₄ aqueous solution (100 mL) and THF (500 mL), and stirred under reflux for about 12 hours. After the reaction was completed, the mixture was cooled to room temperature, and the organic layer was layer separated from the reaction mixture, dried over magnesium sulfate, distilled under reduced pressure, and recrystallized with THF/EtOH to obtain compound B (24 g, 68%).

MS [M ⁺ ] = found 430.99, calc. 430.17

Preparation Example 3: Preparation of Compound C

After dissolving compound B (20.0 g, 46.5 mmol) in chloroform (500 mL), NBS (8.8 g, 48.8 mmol) was added, and the mixture was stirred at room temperature for 12 hours. After completion of the reaction, the solid produced during the reaction was filtered, washed with distilled water and dried to obtain compound C (20.2 g, 85%).

MS [M ⁺ ] = found 508.61, calc. 508.08

Preparation Example 4: Preparation of compound D and HOST-1

Compound C (10g, 19.6 mmol), 4-phenylboronic acid (2.51 g, 20.6 mmol), Pd(t-Bu ₃ P) ₂ (0.15 g, 0.03 mmol) was mixed with 2M K ₂ CO ₃ aqueous solution (30 mL). into THF (100 mL) and stirred at reflux for about 12 hours. After the reaction was completed, it was cooled to room temperature, and the organic layer was separated from the reaction mixture, dried over magnesium sulfate, distilled under reduced pressure, and recrystallized with Tol/EA to obtain compound D (9.2 g, 93%). Then, HOST-1 was prepared by substituting with deuterium in the same manner as in Scheme 2.

MS [M ⁺ ] = found 506.53, calc. 515~533

Compounds A to D and HOST-1 prepared in Preparation Examples 1 to 4 are as follows.

Preparation Example 5: Preparation of compounds E, F, G, H, I, O, P, Q, U, X and preparation of HOST-2, 3, 4, 5, 6, 10, 11, 12, 16, 19

In the same manner as in Preparation Example 4, Compound C (10 g, 19.6 mmol) and 1-naphthalene boronic acid, 1,1-biphenyl-2-boronic acid, 4-dibenzofuran boronic acid, 9,9-diphenyl flu Orene-4-boronic acid, 9,9-spirofluorene-4-boronic acid, 3-indolocarbazole boronic acid, 9,9-dimethyl xanthine-4-boronic acid, 9,9-dimethyl-10 -Phenyl-4-acridine boronic acid, 9-phenyl-4-carbazole boronic acid, 6-naphthobenzofuran boronic acid using compounds E, F, G, H, I, O, P, Q, U, X were prepared.

Then, compound E (8.2 g, 75%), compound F (9.3 g, 81%), compound G (7.5 g, 64%), compound H (9.1 g, 62%), compound I (8.5 g, 58%) ), compound O (8.2 g, 62%), compound P (8.7 g, 69%), compound Q (7.5 g, 54%), compound U (8.1 g, 61%), compound X (8.8 g, 69%) ) was substituted with deuterium in the same manner as in Scheme 2 to obtain HOST-2, 3, 4, 5, 6, 10, 11, 12, 16 and 19.

Preparation Example 6: Preparation of Compound J

Compound J (24 g, 91%) was obtained in the same manner as in Preparation Example 2, except that 4-phenylboronic acid (20.7 g, 170 mmol) was used instead of 1-bromonaphthalene boronic acid.

MS [M ⁺ ] = found 330.67, calc. 330.14

Preparation Example 7: Preparation of Compound K

Compound K (23.5 g, 95%) was obtained in the same manner as in Preparation Example 3, except that Compound J (20g, 60.5 mmol) was used instead of Compound B.

MS [M ⁺ ] = found 409.66, calc. 409.33

Compounds J and K prepared in Preparation Examples 6 and 7 are as follows.

Preparation Example 8: Preparation of compounds L, M, N, V and preparation of HOST-7, 8, 9, 17

In the same manner as in Preparation Example 4, compounds L, M, N and V was made. Then, compound L (6.0 g, 75%), compound M (7.7 g, 86%), compound N (8.2 g, 84%), and compound V (7.0 g, 60%) in the same manner as in Scheme 2, deuterium Substitution gave HOST-7, 8, 9 and 17.

Preparation Example 9: Preparation of compounds R, S, W and preparation of HOST-13, 14, 18

In the same manner as in Preparation Example 4, 1,8-dichloro-10-phenylanthracene (10 g, 30.9 mmol) and 1,1-biphenyl-3-boronic acid, 1,1-biphenyl-2-boronic acid, Compounds R, S and W were prepared using 9,9-diphenylfluorene-4-boronic acid. Thereafter, compound R (9.9 g, 90%), compound S (9.2 g, 84%), and compound W (8.9 g, 51%) were substituted with deuterium in the same manner as in Scheme 2 to obtain HOST-13, 14 and 18 got it

Preparation Example 10: Preparation of compound T and preparation of HOST-15

Compound T (15.6 g, 82%) was prepared using 1,8-dichloro-10-naphthylanthracene (10 g, 26.8 mmol) and 4-phenylnaphthalene-1-boronic acid in the same manner as in Preparation Example 4. . Then, HOST-15 was obtained by substitution with deuterium in the same manner as in Scheme 2.

<Example 1-1>

A glass substrate coated with indium tin oxide (ITO) to a thickness of 1,000 Å was put in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a Fischer Co. product was used as the detergent, and distilled water filtered through a second filter of a Millipore Co. product was used as the distilled water. After washing the ITO for 30 minutes, ultrasonic cleaning was performed twice with distilled water for 10 minutes. After washing with distilled water, ultrasonic cleaning was performed with solvents such as isopropyl alcohol, acetone, and methanol, dried, and transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transferred to a vacuum deposition machine.

Hexanitrile hexaazatriphenylene (HAT) having the following chemical formula was thermally vacuum deposited to a thickness of 500 Å on the prepared ITO transparent electrode to form a hole injection layer.

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

Subsequently, an electron blocking layer was formed by vacuum depositing [HT 2 ] to a film thickness of 50 Å on the hole transport layer.

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

On the light emitting layer, the following ETL and lithium quinolate (LiQ) 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 negative electrode 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 the organic material was maintained at 0.4 to 0.7Å/sec, the deposition rate of lithium fluoride on the cathode was 0.3Å/sec, and the deposition rate of aluminum was 2Å/sec, and the vacuum level during deposition was 2 × 10 ^-7 While maintaining ~5 ⅹ10 ^-6 torr, an organic light emitting device was fabricated.

<Examples 1-2 to 1-19>

An organic light emitting device was manufactured in the same manner as in Example 1-1, except that the compound shown in Table 1 was 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 in Example 1-1, except for using compounds D, E, F, G, and H having the following structures instead of HOST 1 in Example 1-1.

<Comparative Examples 1-6 to 1-10>

In Example 1-1, an organic light-emitting device was manufactured in the same manner as in Example 1-1, except that HOSTs 1 to 5 were used and BD 2 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 at a current density of 20 mA/cm ² was measured. The results are shown in Table 1 below.

compound compound Voltage
(V@10mA/cm ² ) efficiency
(cd/A@10mA/cm ² ) Life (h)
T ₉₀ at 20mA/cm ² Example 1-1 Host 1 BD 1 4.58 5.71 169 Example 1-2 Host 2 BD 1 4.62 5.51 169 Example 1-3 Host 3 BD 1 4.62 5.51 149 Example 1-4 Host 4 BD 1 4.61 5.51 199 Example 1-5 Host 5 BD 1 4.69 5.75 147 Example 1-6 Host 6 BD 1 4.59 5.71 158 Examples 1-7 Host 7 BD 1 4.57 5.71 160 Examples 1-8 Host 8 BD 1 4.58 5.51 169 Examples 1-9 Host 9 BD 1 4.62 5.51 169 Examples 1-10 HOST 10 BD 1 4.62 5.51 169 Example 1-11 HOST 11 BD 1 4.61 5.75 149 Examples 1-12 Host 12 BD 1 4.59 5.71 199 Examples 1-13 Host 13 BD 1 4.57 5.51 147 Examples 1-14 Host 14 BD 1 4.58 5.75 158 Examples 1-15 Host 15 BD 1 4.62 5.71 160 Examples 1-16 Host 16 BD 1 4.62 5.51 169 Examples 1-17 Host 17 BD 1 4.61 5.51 169 Examples 1-18 Host 18 BD 1 4.62 5.51 169 Examples 1-19 Host 19 BD 1 4.61 5.51 169 Comparative Example 1-1 compound D BD 1 4.92 5.51 98 Comparative Example 1-2 compound E BD 1 4.62 5.54 111 Comparative Example 1-3 compound F BD 1 4.61 5.51 112 Comparative Example 1-4 compound G BD 1 4.92 5.52 114 Comparative Example 1-5 compound H BD 1 4.92 5.51 117 Comparative Example 1-6 Host 1 BD 2 4.81 4.95 179 Comparative Example 1-7 Host 2 BD 2 4.71 5.07 178 Comparative Example 1-8 Host 3 BD 2 4.70 4.90 158 Comparative Example 1-9 Host 4 BD 2 4.80 4.98 201 Comparative Example 1-10 Host 5 BD 2 4.81 5.02 158

From the results of Table 1, the organic light emitting device using the deuterium-substituted host represented by HOST 1 to 9 at the same time as BD 1 was Comparative Examples 1-1 to 1-5 using compounds D to H not substituted with deuterium as a host It can be seen that it exhibits better characteristics in terms of driving voltage, efficiency, and lifespan. Such results show that when the compound of Formula 1 and the compound of Formula 2 are used together, while maintaining Forster-energy transfer in which energy is transferred from the host represented by Formula 1 to the dopant, This is because there is an effect of improving life due to enthalpy stability.

In addition, Examples 1-1 to 1-5 using BD 1 as a dopant are compared to Comparative Examples 1-6 to 1-10 using BD 2 as a dopant, showing the effect of increasing efficiency and improving voltage while maintaining lifespan You can check.

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: electron 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)

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

In Formula 1,
Ar1 and Ar2 are the same as or different from each other, and are each independently an aryl group unsubstituted or substituted with one selected from the group consisting of deuterium, an alkyl group and an aryl group,
Ar3 is a deuterium, an aryl group unsubstituted or substituted with one selected from the group consisting of an alkyl group and an aryl group; Or a heterocyclic group unsubstituted or substituted with one selected from the group consisting of heavy hydrogen, an alkyl group and an aryl group,
L1 to L3 are the same as or different from each other, and are each independently a direct bond; An arylene group unsubstituted or substituted with heavy hydrogen; Or a divalent heterocyclic group unsubstituted or substituted with deuterium,
R1 is hydrogen or deuterium;
a to c are each an integer of 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,
r1 is an integer from 0 to 7, and when r1 is 2 or more, R1 are the same as or different from each other;
The compound represented by Formula 1 is 80% or more substituted with deuterium,
[Formula 2]

In Formula 2,
A is a benzene ring,
B and C are two or more aromatic hydrocarbon rings; or a two or more ring heterocycle. delete The organic light emitting device of claim 1, wherein the light emitting layer includes the compound represented by Chemical Formula 1 as a host of the light emitting layer. The organic light emitting device of claim 1, wherein the light emitting layer includes the compound represented by Chemical 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 Chemical Formula 1. The organic light emitting device of claim 1, wherein the emission layer has a maximum emission peak (λ _max ) of 400 nm to 470 nm. delete The method of claim 1,
At least one of B and C is an organic light emitting device represented by any one of Formulas 3 to 7:
[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

In Chemical Formulas 3 to 7, * means a condensed position,
X is O; or S,
G1 and G11 are each independently hydrogen;
g1 and g11 are 6 each. The method of claim 1,
Formula 2 is an organic light emitting device represented by 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 in Formula 2,
X and Y are the same as 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, and g3 is 2. The organic light emitting device of claim 1, wherein the compound represented by Chemical Formula 1 is represented by one of the following compounds:

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


. The method of claim 3,
The organic light emitting device further comprises one or more light emitting layers. The method of claim 12,
The two or more light emitting layers are organic light emitting devices that are different from each other in wavelength bands in which maximum emission peaks appear. The method of claim 12,
The organic 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. The method of claim 14,
An organic light emitting device including a phosphorescent dopant in an emission layer additionally included in addition to the light emitting layer including the compound represented by Formula 1 and the compound represented by Formula 2. The organic light emitting device of claim 12, wherein the two or more light emitting layers are provided vertically or horizontally. The organic light emitting diode of claim 1, wherein the organic light emitting diode further comprises two or more light emitting layers provided vertically, and the three or more light emitting layers are blue fluorescent light emitting layers. The method of claim 1,
The organic material layer further comprises at least one layer 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 Organic light emitting device. The method of claim 17
The organic light emitting device further includes one or more organic material layers 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 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 at least one layer of an electron injection layer, an electron transport and injection layer, and a hole blocking layer.