KR20210141044A - Organic light emitting device - Google Patents

Abstract

The present specification provides an organic light emitting element, which includes: anode; cathode; a light emitting layer provided between the anode and the cathode; a first organic material layer provided between the anode and the light emitting layer; and a second organic material layer provided between the first organic material layer and the light emitting layer, wherein the first organic material layer contains a compound represented by Formula 1. The second organic material layer provides an organic light emitting element comprising a compound represented by Formula 2.

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 combine in the organic thin film to form a pair, and then disappear and emit light. The organic thin film may be composed of a single layer or multiple layers, if necessary.

As materials used in organic light emitting devices, pure organic materials or complex compounds in which organic materials and metals are complexed account for most, and depending on the use, hole injection materials, hole transport materials, light emitting materials, electron transport materials, electron injection materials can be divided into 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 during oxidation, is mainly used. On the other hand, as an electron injection material or an 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 during reduction is mainly used. As the light emitting layer material, a material having both p-type properties 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 formed is preferable.

In order to improve the performance, lifespan or efficiency of an organic light emitting device, the development of a material for an organic thin film is continuously required.

JP 3824385 B2

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

An exemplary embodiment of the present specification is

anode;

cathode;

a light emitting layer provided between the anode and the cathode;

a first organic material layer provided between the anode and the light emitting layer;

and a second organic material layer provided between the first organic material layer and the light emitting layer,

The first organic layer includes a compound represented by Formula 1, and the second organic layer includes a compound represented by Formula 2 below.

[Formula 1]

In Formula 1,

R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; nitrile group; silyl group; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, or a substituted or unsubstituted ring by combining with an adjacent group,

L1 is a direct bond; Or a substituted or unsubstituted arylene group,

Ar1 is a substituted or unsubstituted heterocyclic group,

Ra and Rb are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; nitrile group; silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

a and b are integers from 0 to 7,

when a is 2 or more, two or more Ra are the same as or different from each other, and when b is 2 or more, two or more Rb are the same or different from each other,

[Formula 2]

In Formula 2,

G1 to G3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; nitrile group; silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted ring by combining with an adjacent group,

L2 and L3 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,

Ar2 and Ar3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted aryl group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted arylalkenyl group; Or a substituted or unsubstituted heterocyclic group,

g1 is an integer from 0 to 8, and when g1 is 2 or more, G1 of 2 or more are the same as or different from each other,

g2 and g3 are integers from 0 to 4, and when g2 is 2 or more, two or more G2s are the same as or different from each other, and when g3 is 2 or more, two or more G3's are the same as or different from each other.

In addition, an exemplary embodiment of the present specification provides an organic light emitting device in which the first organic material layer is a hole injection layer or a hole transport layer.

In addition, an exemplary embodiment of the present specification provides an organic light emitting device in which the second organic material layer is an electron blocking layer.

In addition, an exemplary embodiment of the present specification provides an organic light emitting device that further includes one or more light emitting layers.

In addition, according to an exemplary embodiment of the present specification, in the organic light emitting device, one or more organic material layers are additionally provided between the two or more light emitting layers, and the organic material layers include a hole transport layer, a hole injection layer, a hole transport and injection layer, and an electron blocking layer. , It provides an organic light emitting device that further comprises one or more of a charge generating layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron transport and injection layer, and a hole blocking layer.

The organic light emitting device of the present invention includes the compound represented by Formula 1 in the first organic layer and the compound represented by Formula 2 in the second organic layer, thereby having a low driving voltage, high efficiency and/or long life. can get

1 and 2 show an example of an organic light emitting device according to an exemplary embodiment of the present specification.
3 and 4 show examples of an organic light emitting device including two or more stacks.

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

The present specification is anode; cathode; a light emitting layer provided between the anode and the cathode; a first organic material layer provided between the anode and the light emitting layer; and a second organic material layer provided between the first organic material layer and the light emitting layer, wherein the first organic material layer includes a compound represented by the following Chemical Formula 1, and the second organic material layer is represented by the following Chemical Formula 2 It provides an organic light emitting device comprising a compound to be.

[Formula 1]

In Formula 1,

R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; nitrile group; silyl group; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, or a substituted or unsubstituted ring by combining with an adjacent group,

L1 is a direct bond; Or a substituted or unsubstituted arylene group,

Ar1 is a substituted or unsubstituted heterocyclic group,

Ra and Rb are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; nitrile group; silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

a and b are integers from 0 to 7,

when a is 2 or more, two or more Ra are the same as or different from each other, and when b is 2 or more, two or more Rb are the same or different from each other,

[Formula 2]

In Formula 2,

G1 to G3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; nitrile group; silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted ring by combining with an adjacent group,

L2 and L3 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,

Ar2 and Ar3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted aryl group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted arylalkenyl group; Or a substituted or unsubstituted heterocyclic group,

g1 is an integer from 0 to 8, and when g1 is 2 or more, G1 of 2 or more are the same as or different from each other,

g2 and g3 are integers from 0 to 4, and when g2 is 2 or more, two or more G2s are the same as or different from each other, and when g3 is 2 or more, two or more G3's are the same as or different from each other.

Formula 1 of the present invention is a structure in which a fluorenyl group and a heterocyclic group (Ar1) are bonded through an amine group at the 2nd position of the fluorene-based core, and Formula 2 of the present invention is a biphenylene linker and a carbazole connected in an ortho direction When the compound represented by Formula 1 and the compound represented by Formula 2 are used as the monoamine structure, there is an advantage in that the driving voltage and luminous efficiency of the organic light emitting device, in particular, the lifespan characteristics are improved.

In the present specification, when a part "includes" a certain component, this means that other components may be further included rather than excluding other components unless otherwise stated.

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

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

In the present specification, the meaning that a specific material A is included in layer B means that i) one or more types of material A are included in one layer B, and ii) layer B is composed of one or more layers, and material A is multi-layered B. It includes everything included in one or more floors among the floors.

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

"는 화학식 또는 화합물에 결합되는 위치를 의미한다.In this specification, "

" means the position 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 position at which the hydrogen atom is substituted, that is, a position where the substituent is substitutable, is substituted. , two or more substituents may be the same as or different from each other.

As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imid; 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 it means that it is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group, is substituted with a substituent to which two or more of the above-exemplified substituents are connected, or does not have any substituents. 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.

As used herein, the term "substituted or unsubstituted" refers to a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group, is substituted with a substituent to which two or more of the above-exemplified substituents are connected, or does not have any substituents.

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 the 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, but is not limited to, 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. does not

In the present specification, the boron group may be represented by the formula of _{-BY d} Y _{e , wherein Y d} and Y _e are hydrogen; a substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. Specifically, the boron group includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group.

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

In the present specification, the alkoxy group may be a straight chain, branched chain or cyclic chain. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C20. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n -hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy and the like may be used, but is not limited thereto.

The substituents containing an alkyl group, an alkoxy group and other alkyl group moieties described herein include both straight-chain or pulverized 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 carbon number of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. 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 is not limited thereto.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 30. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 20. The aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, a terphenyl group, or a quaterphenyl 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 aryl group is a monocyclic to six rings. According to an exemplary embodiment, the aryl group is monocyclic to tetracyclic. According to another exemplary embodiment, the aryl group is monocyclic to tricyclic.

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

,

등의 스피로플루오레닐기,

(9,9-디메틸플루오레닐기), 및

(9,9-디페닐플루오레닐기) 등의 치환된 플루오레닐기가 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

spirofluorenyl groups such as

(9,9-dimethyl fluorenyl group), and

a substituted fluorenyl group such as (9,9-diphenylfluorenyl group). However, the present invention is not limited thereto.

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

In the present specification, the heterocyclic group is a cyclic group including at least one of N, O, P, S, Si and Se as a heteroatom, and the number of carbon atoms is not particularly limited, but it is preferably from 2 to 60 carbon atoms. According to an exemplary embodiment, the heterocyclic group has 2 to 30 carbon atoms. Examples of the heterocyclic group include 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, a dibenzothiophene group , a carbazole group, a benzocarbazole group, a naphthobenzofuran group, a benzonaphthothiophene group, an indenocarbazole group, and the like, but are not limited thereto.

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

In the present specification, in a substituted or unsubstituted ring formed by bonding with an adjacent group, "ring" is a hydrocarbon ring; or a heterocyclic ring.

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

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

The heterocyclic ring may be applied to the description of the heterocyclic group.

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

Hereinafter, the formula (1) will be described in detail.

According to an exemplary embodiment of the present specification, R1 to R4 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or a substituted or unsubstituted ring by combining with an adjacent group.

According to an exemplary embodiment of the present specification, R1 to R4 are the same as or different from each other, and each independently a substituted or unsubstituted C 1 to C 60 alkyl group; Or a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted C2-C60 ring by combining with an adjacent group.

According to an exemplary embodiment of the present specification, R1 to R4 are the same as or different from each other, and each independently a substituted or unsubstituted C 1 to C 30 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring having 2 to 30 carbon atoms by combining with an adjacent group.

According to an exemplary embodiment of the present specification, R1 to R4 are the same as or different from each other, and each independently a substituted or unsubstituted C 1 to C 20 alkyl group; Or a substituted or unsubstituted C6-C20 aryl group, or a substituted or unsubstituted C2-C20 ring by combining with an adjacent group.

According to an exemplary embodiment of the present specification, R1 to R4 are the same as or different from each other, and each independently a substituted or unsubstituted methyl group; or a substituted or unsubstituted phenyl group, or a substituted or unsubstituted fluorene ring by combining with an adjacent group.

According to an exemplary embodiment of the present specification, R1 to R4 are the same as or different from each other, and each independently a methyl group; or a phenyl group, or a fluorene ring by bonding with adjacent groups.

According to an exemplary embodiment of the present specification, L1 is a direct bond; or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

According to an exemplary embodiment of the present specification, L1 is a direct bond; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L1 is a direct bond; or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, L1 is a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted anthracenylene group; a substituted or unsubstituted phenanthrenylene group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted phenalene group; or a substituted or unsubstituted pyrene group.

According to an exemplary embodiment of the present specification, L1 is a direct bond; a substituted or unsubstituted phenylene group; Or a substituted or unsubstituted biphenylene group.

According to an exemplary embodiment of the present specification, L1 is a direct bond; phenylene group; or a biphenylene group.

According to an exemplary embodiment of the present specification, L1 is a direct bond; or a phenylene group.

According to an exemplary embodiment of the present specification, L1 is a direct bond.

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

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

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

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

According to an exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted carbazole group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.

According to an exemplary embodiment of the present specification, Ar1 is a carbazole group unsubstituted or substituted with a phenyl group; a dibenzofuran group unsubstituted or substituted with a phenyl group; or a dibenzothiophene group unsubstituted or substituted with a phenyl group.

According to an exemplary embodiment of the present specification, Ar1 is a carbazole group unsubstituted or substituted with a phenyl group; dibenzofuran group; or a dibenzothiophene group.

According to an exemplary embodiment of the present specification, Ar1 is a dibenzofuran group; or a dibenzothiophene group.

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

[Formula 1-1]

[Formula 1-2]

In Formulas 1-1 and 1-2,

The definitions of R1 to R4, Ra, Rb, L1, a and b are the same as the definitions in Formula 1 above,

X is O; S; or NR;

R, Rc and Rd are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; nitrile group; silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

c is an integer from 0 to 7,

d is an integer from 0 to 8,

When c is 2 or more, two or more Rc are the same as or different from each other, and when d is 2 or more, two or more Rd are the same or different from each other.

According to an exemplary embodiment of the present specification, X is O; or S.

According to an exemplary embodiment of the present specification, X is NR.

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

According to an exemplary embodiment of the present specification, R is a substituted or unsubstituted C 2 to C 60 aryl group.

According to an exemplary embodiment of the present specification, R is a substituted or unsubstituted aryl group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, R is a substituted or unsubstituted aryl group having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, R is a substituted or unsubstituted phenyl group.

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

According to an exemplary embodiment of the present specification, Rc and Rd are the same as or different from each other, and each independently hydrogen; or deuterium.

According to an exemplary embodiment of the present specification, Rc and Rd are hydrogen.

According to an exemplary embodiment of the present specification, c and d are 0.

According to an exemplary embodiment of the present specification, c and d are 1.

According to an exemplary embodiment of the present specification, c is 7.

According to an exemplary embodiment of the present specification, d is 8.

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

According to an exemplary embodiment of the present specification, Ra and Rb are the same as or different from each other, and each independently hydrogen; or deuterium.

According to an exemplary embodiment of the present specification, Ra and Rb are hydrogen.

According to an exemplary embodiment of the present specification, a and b are 0.

According to an exemplary embodiment of the present specification, a and b are 1.

According to an exemplary embodiment of the present specification, a and b are 7.

According to an exemplary embodiment of the present specification, Chemical Formula 1-1 is represented by any one of the following Chemical Formulas 1-3 to 1-6.

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

In Formulas 1-3 to 1-6,

Definitions of R1 to R4, Ra, Rb, Rc, L1, a, b, c, and X are the same as those in Formula 1-1.

Hereinafter, the formula (2) will be described in detail.

According to an exemplary embodiment of the present specification, the G1 to G3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; nitrile group; silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted ring by combining with an adjacent group.

According to an exemplary embodiment of the present specification, the G1 to G3 are the same as or different from each other, and each independently hydrogen; or deuterium, or a substituted or unsubstituted C6-C60 ring by combining with an adjacent group.

According to an exemplary embodiment of the present specification, the G1 to G3 are the same as or different from each other, and each independently hydrogen; or deuterium, or a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms by combining with adjacent groups.

According to an exemplary embodiment of the present specification, the G1 to G3 are the same as or different from each other, and each independently hydrogen; or deuterium, or a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 20 carbon atoms by combining with adjacent groups.

According to an exemplary embodiment of the present specification, the G1 to G3 are the same as or different from each other, and each independently hydrogen; or deuterium, or combined with adjacent groups to form a substituted or unsubstituted benzene ring.

According to an exemplary embodiment of the present specification, G1 to G3 are the same as or different from each other, and are each independently hydrogen, or combine with adjacent groups to form a benzene ring.

According to an exemplary embodiment of the present specification, the G1 to G3 are the same as or different from each other, and each independently hydrogen; or deuterium.

According to an exemplary embodiment of the present specification, G1 to G3 are hydrogen.

According to an exemplary embodiment of the present specification, G1 is hydrogen, or a substituted or unsubstituted benzene ring is formed by bonding with an adjacent group.

According to an exemplary embodiment of the present specification, G1 is hydrogen, or a benzene ring is formed by bonding with an adjacent group.

According to an exemplary embodiment of the present specification, G2 and G3 are the same as or different from each other, and each independently hydrogen; or deuterium.

According to an exemplary embodiment of the present specification, G2 and G3 are hydrogen.

According to an exemplary embodiment of the present specification, L2 and L3 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

According to an exemplary embodiment of the present specification, L2 and L3 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L2 and L3 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, L2 and L3 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted fluorenylene group; a substituted or unsubstituted phenanthrenylene group; Or a substituted or unsubstituted triphenylene group.

According to an exemplary embodiment of the present specification, L2 and L3 are the same as or different from each other, and each independently a direct bond; a phenylene group unsubstituted or substituted with a methyl group or a phenyl group; a biphenylene group unsubstituted or substituted with a methyl group or a phenyl group; a naphthylene group unsubstituted or substituted with a methyl group or a phenyl group; a fluorenylene group unsubstituted or substituted with a methyl group or a phenyl group; a phenanthrenylene group unsubstituted or substituted with a methyl group or a phenyl group; or a triphenylene group unsubstituted or substituted with a methyl group or a phenyl group.

According to an exemplary embodiment of the present specification, L2 and L3 are the same as or different from each other, and each independently a direct bond; phenylene group; biphenylene group; naphthylene group; a fluorenylene group unsubstituted or substituted with a methyl group or a phenyl group; phenanthrenylene group; or a triphenylene group.

According to an exemplary embodiment of the present specification, L2 and L3 are the same as or different from each other, and each independently a direct bond; phenylene group; biphenylene group; naphthylene group; or a fluorenylene group unsubstituted or substituted with a methyl group or a phenyl group.

According to an exemplary embodiment of the present specification, L2 and L3 are the same as or different from each other, and each independently a direct bond; phenylene group; biphenylene group; naphthylene group; dimethyl fluorenylene group; or a diphenylfluorenylene group.

According to an exemplary embodiment of the present specification, L2 and L3 are the same as or different from each other, and each independently a direct bond; or a phenylene group.

According to an exemplary embodiment of the present specification, L2 and L3 are a direct bond.

According to an exemplary embodiment of the present specification, Ar2 and Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

According to an exemplary embodiment of the present specification, Ar2 and Ar3 are the same as or different from each other, and each independently 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.

According to an exemplary embodiment of the present specification, Ar2 and Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar2 and Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted C6-C20 aryl group; Or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, Ar2 and Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted triphenylenyl group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.

According to an exemplary embodiment of the present specification, Ar2 and Ar3 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a methyl group or a phenyl group; a biphenyl group unsubstituted or substituted with a methyl group or a phenyl group; a terphenyl group unsubstituted or substituted with a methyl group or a phenyl group; a naphthyl group unsubstituted or substituted with a methyl group or a phenyl group; a fluorenyl group unsubstituted or substituted with a methyl group or a phenyl group; a phenanthrenyl group unsubstituted or substituted with a methyl group or a phenyl group; a triphenylenyl group unsubstituted or substituted with a methyl group or a phenyl group; a dibenzofuran group unsubstituted or substituted with a methyl group or a phenyl group; or a dibenzothiophene group unsubstituted or substituted with a methyl group or a phenyl group.

According to an exemplary embodiment of the present specification, Ar2 and Ar3 are the same as or different from each other, and each independently a phenyl group; biphenyl group; terphenyl group; naphthyl group; a fluorenyl group unsubstituted or substituted with a methyl group or a phenyl group; phenanthrenyl group; triphenylenyl group; dibenzofuran group; or a dibenzothiophene group.

According to an exemplary embodiment of the present specification, Ar2 and Ar3 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a phenanthrenyl group; a naphthyl group unsubstituted or substituted with a phenyl group; or a phenanthrenyl group.

According to an exemplary embodiment of the present specification, Ar2 and Ar3 are the same as or different from each other, and each independently a phenyl group; a naphthyl group unsubstituted or substituted with a phenyl group; or a phenanthrenyl group.

According to an exemplary embodiment of the present specification, g1 is 0.

According to an exemplary embodiment of the present specification, g1 is 1.

According to an exemplary embodiment of the present specification, g1 is 2.

According to an exemplary embodiment of the present specification, g1 is 8.

According to an exemplary embodiment of the present specification, g2 and g3 are 0.

According to an exemplary embodiment of the present specification, g2 and g3 are 1.

According to an exemplary embodiment of the present specification, g2 and g3 are 4.

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

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

In Formulas 2-1 to 2-4,

The definitions of L2, L3, Ar2, Ar3, G2, G3, g2 and g3 are the same as those in Formula 2 above,

G11 and G12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; nitrile group; silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

g11 is an integer from 0 to 8, and when g11 is 2 or more, 2 or more G11 are the same as or different from each other,

g12 is an integer from 0 to 10, and when g12 is 2 or more, two or more G12s are the same as or different from each other.

According to an exemplary embodiment of the present specification, G11 and G12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

According to an exemplary embodiment of the present specification, G11 and G12 are the same as or different from each other, and each independently hydrogen; or deuterium.

According to an exemplary embodiment of the present specification, G11 and G12 are hydrogen.

According to an exemplary embodiment of the present specification, g11 is 0.

According to an exemplary embodiment of the present specification, g11 is 1.

According to an exemplary embodiment of the present specification, g11 is 8.

According to an exemplary embodiment of the present specification, g12 is 0.

According to an exemplary embodiment of the present specification, g12 is 1.

According to an exemplary embodiment of the present specification, g12 is 10.

According to an exemplary embodiment of the present specification, Chemical Formula 2 is represented by any one of the following Chemical Formulas 2-5 to 2-7.

[Formula 2-5]

[Formula 2-6]

[Formula 2-7]

In Formulas 2-5 to 2-7,

The definitions of L2, L3, Ar2, Ar3, G1 to G3, and g1 to g3 are the same as in Formula 2 above.

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

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

The compound according to an exemplary embodiment of the present specification may be prepared by a manufacturing method described below. If necessary, a substituent may be added or excluded, and the position of the substituent may be changed. In addition, based on techniques known in the art, starting materials, reactants, reaction conditions, and the like can be changed.

Hereinafter, an organic light emitting device will be described.

An organic light emitting device according to the present specification includes an anode; cathode; a light emitting layer provided between the anode and the cathode; a first organic material layer provided between the anode and the light emitting layer; and a second organic material layer provided between the first organic material layer and the light emitting layer, wherein the first organic material layer includes the compound represented by Formula 1, and the second organic material layer is represented by Formula 2 It is characterized in that it contains a compound that becomes

The organic light emitting device of the present invention is a conventional organic light emitting device, except that the first organic layer is formed using the compound represented by Formula 1 and the second organic layer is formed using the compound of Formula 2 described above. It can be manufactured by the manufacturing method and material of

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

The organic material layer of the organic light emitting device of the present specification may have a structure including only the first organic material layer and the second organic material layer, or may have a structure further including an additional organic material layer. The additional organic material layer may be one or more of a hole injection layer, a hole transport 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. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number or a larger number of organic material layers.

In the organic light emitting device according to the exemplary embodiment of the present specification, the first organic material layer is provided between the light emitting layer and the anode.

In the organic light emitting device according to an exemplary embodiment of the present specification, the first organic material layer includes a hole injection layer, a hole transport layer, an electron blocking layer, or a hole transport and injection layer, and the hole injection layer, the hole transport layer, the electron blocking layer , or the hole transport and injection layer may include a compound represented by the above-described formula (1).

In the organic light emitting device according to an exemplary embodiment of the present specification, the first organic material layer includes a hole injection layer, a hole transport layer, or a hole transport and injection layer, and the hole injection layer, the hole transport layer or the hole transport and injection layer is the above-described The compound represented by Formula 1 may be included.

In the organic light emitting device according to an exemplary embodiment of the present specification, the first organic material layer may include a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer may include the compound represented by Formula 1 described above.

In the organic light emitting device according to an exemplary embodiment of the present specification, the first organic material layer may be a hole transport layer, and the hole transport layer may include the compound represented by Chemical Formula 1 described above.

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

In the organic light emitting device according to an exemplary embodiment of the present specification, the first organic material layer is a hole injection layer or a hole transport layer, and the organic light emitting device further includes at least one hole injection layer or a hole transport layer in addition to the first organic material layer, and each hole The injection layer or the hole transport layer may include a compound represented by Formula 1 above.

In the organic light emitting device according to an exemplary embodiment of the present specification, the first organic material layer is a hole transport layer, and the organic light emitting device further includes one or more hole transport layers in addition to the first organic material layer, and each hole transport layer is represented by Formula 1 compounds may be included.

In the organic light emitting device according to an exemplary embodiment of the present specification, the organic material layer may include two or more hole injection layers, hole transport layers, or electron blocking layers.

In the organic light emitting device according to the exemplary embodiment of the present specification, the organic material layer may include two or more hole transport layers.

In the organic light emitting device according to the exemplary embodiment of the present specification, the organic material layer may include three or more hole injection layers, hole transport layers, or electron blocking layers.

In the organic light emitting device according to the exemplary embodiment of the present specification, the organic material layer may include three or more hole transport layers.

In the organic light emitting device according to an exemplary embodiment of the present specification, the second organic material layer includes a hole injection layer, a hole transport layer, an electron blocking layer, or a hole transport and injection layer, and the hole injection layer, the hole transport layer, the electron blocking layer , or the hole transport and injection layer may include a compound represented by the above-described formula (2).

In the organic light emitting device according to an exemplary embodiment of the present specification, the second organic material layer may include a hole transport layer or an electron blocking layer, and the hole transport layer or the electron blocking layer may include a compound represented by the above-described Chemical Formula 2.

In the organic light emitting device according to an exemplary embodiment of the present specification, the second organic material layer may be an electron blocking layer, and the electron blocking layer may include the compound represented by Chemical Formula 2 described above.

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

In the organic light emitting device according to an exemplary embodiment of the present specification, the second organic material layer is an electron blocking layer, and the organic light emitting device further includes one or more electron blocking layers in addition to the second organic material layer, and each electron blocking layer is represented by Formula 2 It may include a compound represented by.

In the organic light emitting device according to the exemplary embodiment of the present specification, the organic material layer may include two or more electron blocking layers.

In the organic light emitting device according to the exemplary embodiment of the present specification, the organic material layer may include three or more electron blocking layers.

In the organic light emitting device according to an exemplary embodiment of the present specification, the first organic material layer is a hole transport layer, and the second organic material layer is an electron blocking layer.

In the organic light emitting device according to the exemplary embodiment of the present specification, the second organic material layer is provided in contact with the first organic material layer. Here, the contact means that another organic material layer does not exist between the first organic material layer and the second organic material layer.

In the organic light emitting device according to the exemplary embodiment of the present specification, the second organic material layer is provided in contact with the light emitting layer. Here, the contact means that another organic material layer does not exist between the second organic material layer and the light emitting layer.

In the organic light emitting device according to an exemplary embodiment of the present specification, the compound represented by the above-described Formula 1 included in the first organic layer and the compound represented by the aforementioned Formula 2 included in the second organic layer are different from each other.

The organic light emitting device according to an exemplary embodiment of the present specification includes a light emitting layer, and the light emitting layer may include a condensed aromatic ring derivative or a heterocyclic compound as a host, but is not limited thereto.

In another exemplary embodiment, the light emitting layer may further include other organic compounds, metals, or metal compounds in addition to the above-described host.

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

In this case, as the dopant, a _{phosphorescent material such as (4,6-F2ppy) 2} Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), distrylarylene (DSA), PFO-based polymer, PPV-based polymer A fluorescent material such as a polymer, an anthracene-based compound, a pyrene-based compound, or a boron-based compound may be used, but is not limited thereto.

The organic light emitting device according to an exemplary embodiment of the present specification further includes one or more light emitting layers in addition to the light emitting layer, and each light emitting layer may include the above-described host compound.

The organic light emitting device according to an exemplary embodiment of the present specification further includes one or more light emitting layers in addition to the light emitting layer, and each light emitting layer further includes a fluorescent dopant or a phosphorescent dopant. In this case, the dopant in the emission layer is included in an amount of 1 to 50 parts by weight based on 100 parts by weight of the host.

In the organic light emitting device according to the exemplary embodiment of the present specification, the organic material layer may include two or more light emitting layers.

In the organic light emitting device according to the exemplary embodiment of the present specification, the organic material layer may include three or more light emitting layers.

In the organic light emitting diode according to the exemplary embodiment of the present specification, the maximum emission peak of the emission layer is 400 nm to 500 nm.

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

The 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 the other layer (light emitting layer 2) The maximum emission peak is 510 nm to 580 nm; Alternatively, the maximum emission peak of 610 nm and 680 nm may be exhibited, and the maximum emission peak of the emission layer (emission layer 3) of another layer may exhibit a maximum emission peak of 400 nm to 500 nm.

In the organic light emitting device according to an exemplary embodiment of the present specification, one or more organic material layers are additionally provided between the anode and the cathode, and the organic material layers include a hole transport layer, a hole injection layer, a hole transport and injection layer, an electron blocking layer, and a light emitting layer. , may further include one or more of an electron transport layer, an electron injection layer, an electron transport and injection layer, and a hole blocking layer.

The organic light emitting device according to an exemplary embodiment of the present specification includes at least one light emitting layer, and at least one organic material layer is additionally provided between the at least one light emitting layer, and the organic material layer includes a hole transport layer, a hole injection layer, a hole transport and At least one of an injection layer, an electron blocking layer, a charge generating 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 the exemplary 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 the exemplary embodiment of the present specification, the organic light emitting device may be an inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.

The organic light emitting device may have, for example, a stacked structure as follows, but is not limited thereto.

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

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

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

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

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

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

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

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

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

(10) anode / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / cathode

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

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

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

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

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

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

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

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 shows a substrate 1, an anode 2, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, a hole blocking layer 7, an electron transport and injection layer 8, and a cathode 11 ) of the sequentially stacked organic light emitting device is exemplified. In such a structure, the compound represented by Formula 1 may be included in the hole transport layer 4 , and the compound represented by Formula 2 may be included in the electron blocking layer 5 .

2 shows a substrate 1, an anode 2, a hole transport layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, a hole blocking layer 7, an electron transport layer 9, The structure of the organic light emitting device in which the electron injection layer 10 and the cathode 11 are sequentially stacked is exemplified. In such a structure, the compound represented by Formula 1 may be included in the hole injection layer 3 and the hole transport layer 4 , and the compound represented by Formula 2 may be included in the electron blocking layer 5 .

According to an exemplary embodiment of the present specification, the organic light emitting device may have a tandem structure in which two or more independent devices are connected in series. In an exemplary embodiment, the tandem structure may have a form in which each organic light emitting device is bonded to a charge generating layer. Since the device of the tandem structure can be driven at a lower current than the unit device based on the same brightness, the lifespan characteristics of the device are greatly improved.

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

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

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 and injection layer. It may further include one or more layers of the layer, and the electron transport and injection layer.

An organic light emitting diode including the first stack and the second stack is illustrated in FIG. 3 .

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

An organic light emitting diode including the first to third stacks is illustrated in FIG. 4 .

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

The N-type charge generation layer is 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4TCNQ), fluorine-substituted 3,4,9,10-pe Lylenetetracarboxylic dianhydride (PTCDA), cyano-substituted PTCDA, naphthalenetetracarboxylic dianhydride (NTCDA), fluorine-substituted NTCDA, cyano-substituted NTCDA, hexaazatriphenylline derivatives and the like, but is not limited thereto. In one embodiment, the N-type charge generation layer may include a benzimidazophenanthrine-based derivative and a metal of Li at the same time.

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

For example, the organic light emitting device according to the present specification uses a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, to form a metal or a conductive metal oxide or an alloy thereof on a substrate. is deposited to form an anode, and 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 is formed thereon, and then a material that can be used as a cathode is deposited thereon. can be In addition to this method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

The organic material layer may further include at least one of a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole transport and injection layer.

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

The anode is an electrode for injecting holes, and the anode material is usually preferably a material having a large work function 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, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO ₂ : Combination of metals and oxides such as Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

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

The hole injection layer is a layer that facilitates the injection of holes from the anode to the light emitting layer. As the hole injection material, holes can be well injected from the anode at a low voltage, and the highest occupied (HOMO) of the hole injection material is The molecular orbital) is preferably between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include the above compound or metal porphyrine, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, perylene (perylene)-based organic material, anthraquinone, polyaniline, and polythiophene-based conductive polymer, but is not limited thereto. The hole injection layer may have a thickness of 1 to 150 nm. When the thickness of the hole injection layer is 1 nm or more, there is an advantage that can prevent the hole injection characteristics from being deteriorated, and when it is 150 nm or less, the thickness of the hole injection layer is too thick, so that the driving voltage is increased to improve hole movement There are advantages to avoiding this.

The hole transport layer may serve to facilitate 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 is suitable, and a material having high hole mobility is suitable. Specific examples include, but are not limited to, the above-described compound or an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.

An additional hole buffer layer may be provided between the hole injection layer and the hole transport layer, and may include the aforementioned compound or 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. The above-described compound or a material known in the art may be used for the electron blocking 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-hydroxybenzo quinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene, rubrene, and the like, but is not limited thereto.

Examples of the host material of the light emitting layer include a condensed aromatic ring derivative or a heterocyclic compound containing compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

When the emission layer emits red light, the emission dopant is PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium) ), a phosphorescent material such as octaethylporphyrin platinum (PtOEP), or a _{fluorescent material such as Alq 3} (tris(8-hydroxyquinolino)aluminum) may be used, but is not limited thereto. When the light-emitting layer emits green light, the light-emitting dopant is a _{phosphor such as Ir(ppy) 3} (fac tris(2-phenylpyridine)iridium), Alq3(tris(8-hydroxyquinolino)aluminum), anthracene-based compound, or pyrene-based compound. A fluorescent material such as a compound or a boron-based compound may be used, but is not limited thereto. When the light emitting layer emits blue light, the light emitting dopant includes a _{phosphorescent material such as (4,6-F2ppy) 2} Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), distrylarylene (DSA), A fluorescent material such as a PFO-based polymer, a PPV-based polymer, an anthracene-based compound, a pyrene-based compound, or a boron-based compound may be used, but is 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 the transport of electrons. As the electron transport material, a material capable of well injecting electrons from the cathode and transferring them to the light emitting layer, and a material having high electron mobility is suitable. Specific examples include the Al complex 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 that the electron transport properties can be prevented from being lowered, and if it is 50 nm or less, the thickness of the electron transport layer is too thick to prevent the driving voltage from being increased to improve the movement of electrons. There are advantages that can be

The electron injection layer may serve to facilitate injection of electrons. The electron injection material has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, prevents the movement of excitons generated in the light emitting layer to the hole injection layer, and , a compound having excellent thin film forming ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc., derivatives thereof, 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) ( o-crezolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. However, the present invention is not limited thereto.

The hole blocking layer is a layer that blocks the 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 complex, and the like, but is not limited thereto.

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

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

Preparation Example 1: Preparation of compound 1-1

Compound 3-bromodibenzo [b, d] furan (7.56 g, 19.29 mmol), and compound a-1 in a 500 mL round-bottom flask under nitrogen atmosphere, xylene (Xylene) ) was completely dissolved in 220 mL, NaOtBu (2.22 g, 23.14 mmol) was added, and bis(tri-tert-butylphosphine)palladium(0)(Bis(tri- tert- butylphosphine)palladium(0))(0.10 g) , 0.19 mmol) and stirred with heating for 4 hours. After lowering the temperature to room temperature and filtering to remove the base, Xylene was concentrated under reduced pressure and recrystallized from 180 mL of ethyl acetate to prepare Compound 1-1 (10.12 g, yield: 78%).

MS[M+H] ⁺ = 692

Preparation Example 2: Preparation of compound 1-2

Compound 2-bromodibenzo[b,d]thiophene (6.27 g, 23.84 mmol), and compound a-2 (13.71 g, 26.22 mmol) was completely dissolved in 250 mL of xylene, NaOtBu (2.98 g, 30.99 mmol) was added, and bis(tri-tert-butylphosphine)palladium(0)(Bis(tri- tert- butylphosphine) After adding palladium (0)) (0.24 g, 0.48 mmol), the mixture was heated and stirred for 6 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 250 ml of ethyl acetate to prepare Compound 1-2 (8.74 g, 52%).

MS[M+H] ⁺ = 706

Preparation Example 3: Preparation of compound 1-3

Compound 4- (4-bromophenyl) dibenzo [b, d] furan (4- (4-bromophenyl) dibenzo [b, d] furan) (7.24 g, 22.41 mmol) in a 500 mL round bottom flask under nitrogen atmosphere , and compound a-3 (9.89 g, 24.66 mmol) was completely dissolved in 250 mL of xylene, and NaOtBu (2.22 g, 23.14 mmol) was added thereto, and bis (tri-tert-butylphosphine) palladium (0) ) (Bis(tri- tert- butylphosphine) palladium(0))(0.23 g, 0.45 mmol) was added, followed by heating and stirring for 5 hours. After lowering the temperature to room temperature and filtering to remove the base, Xylene was concentrated under reduced pressure and recrystallized from 230 mL of ethyl acetate to prepare compound 1-3 (9.17 g, yield: 64%).

MS[M+H] ⁺ = 644

Preparation Example 4: Preparation of compound 2-1

Compound b-1 (12.32 g, 20.50 mmol), (2-(9H-carbazol-9-yl)phenyl)boronic acid ((2-(9H-carbazol-9-yl) )phenyl)boronic acid) (6.47g, 22.55mmol) was completely dissolved in 240ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (120ml) was added, and tetrakis-(triphenylphosphine)palladium (0.42g, 0.37) mmol) was added, and the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 350 ml of ethyl acetate to prepare compound 2-1 (11.29 g, 72%).

MS[M+H] ⁺ = 663

Preparation Example 5: Preparation of compound 2-2

Compound b-2 (11.09 g, 19.25 mmol), (2-(9H-carbazol-9-yl)phenyl)boronic acid ((2-(9H-carbazol-9-yl) )phenyl)boronic acid) (6.08 g, 21.18 mmol) was completely dissolved in 240 ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (120 ml) was added, and tetrakis-(triphenylphosphine)palladium (0.67 g, 0.58) mmol) was added, and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 250 ml of ethyl acetate to prepare Compound 2-2 (8.88 g, 62%).

MS[M+H] ⁺ = 689

Preparation Example 6: Preparation of compound 2-3

Compound b-3 (10.55 g, 19.11 mmol), (2-(9H-carbazol-9-yl)phenyl)boronic acid ((2-(9H-carbazol-9-yl) )phenyl)boronic acid) (6.03g, 21.02 mmol) was completely dissolved in 240 ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (120 ml) was added, and tetrakis-(triphenylphosphine)palladium (0.66g, 0.57) mmol) was added, and the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 280 ml of ethyl acetate to prepare compound 2-3 (9.07 g, 66%).

MS[M+H] ⁺ = 689

Comparative Example 1

A glass substrate coated with indium tin oxide (ITO) to a thickness of 1,000 Å was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a product manufactured by Fischer Co. was used as the detergent, and distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water. After washing ITO for 30 minutes, ultrasonic cleaning was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

A hole injection layer was formed by thermally vacuum-depositing the compound of the following compound HI-1 and the compound of the following compound HI-2 to a thickness of 100 Å in a ratio of 98:2 (molar ratio) on the prepared ITO transparent electrode.

The following compound HT-1 (1150 Å), which is a material for transporting holes, was vacuum deposited on the hole injection layer to form a hole transport layer.

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

Then, the compound represented by the following formula BH-1 and the compound represented by the following formula BD-1 to a film thickness of 200 Å on the electron blocking layer were vacuum-deposited in a weight ratio of 25:1 to form a light emitting layer. A hole blocking layer was formed by vacuum-depositing the following compound HB-1 to a thickness of 50 Å on the light emitting layer.

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

In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.7 Å/sec, the deposition rate of lithium fluoride of the negative electrode was maintained at 0.3 Å/sec, and the deposition rate of aluminum was maintained at 2 Å/sec, and the vacuum degree during deposition was 2 × 10 ^-7 to 5 x 10 ^-6 torr, an organic light emitting device was manufactured.

The compound used in Comparative Example 1 is as follows.

Examples 1 to 9 and Comparative Examples 2 to 19

An organic light emitting diode was manufactured in the same manner as in Comparative Example 1, except that the compounds shown in Table 1 were used instead of the hole transport layer compound HT-1 and the electron blocking layer compound EB-1 in Comparative Example 1. The compounds used in the Examples and Comparative Examples are as follows.

^{When a current of 20 mA/cm 2} was applied to the organic light-emitting devices prepared in Examples and Comparative Examples, the driving voltage, luminous efficiency, and color coordinates were obtained for the organic light-emitting device prepared above ^{at a current density of 20 mA/cm 2} was measured, and the time (T95) at which it became 95% of the initial luminance at a current density of ^{20 mA/cm 2 was measured.} The results are shown in Table 1 below. T95 denotes a time required for the luminance to decrease from the initial luminance (1600 nit) to 95%.

compound
(hole transport layer) compound
(electron blocking layer) Voltage
(V
@20mA
/cm ² ) efficiency
(cd/A
@20mA
/cm ² ) color coordinates
(x,y) T95
(hr) Example 1 1-1 2-1 3.63 6.71 (0.146, 0.047) 335 Example 2 1-2 2-1 3.52 6.82 (0.146, 0.046) 350 Example 3 1-3 2-1 3.75 6.67 (0.147, 0.045) 345 Example 4 1-1 2-2 3.67 6.79 (0.146, 0.046) 335 Example 5 1-2 2-2 3.59 6.88 (0.145, 0.045) 350 Example 6 1-3 2-2 3.74 6.61 (0.146, 0.046) 325 Example 7 1-1 2-3 3.68 6.74 (0.146, 0.046) 335 Example 8 1-2 2-3 3.51 6.85 (0.146, 0.046) 350 Example 9 1-3 2-3 3.75 6.60 (0.147, 0.045) 320 Comparative Example 1 HT-1 EB-1 4.40 5.86 (0.146, 0.045) 175 Comparative Example 2 HT-2 2-1 4.03 6.03 (0.145, 0.046) 260 Comparative Example 3 HT-2 2-2 4.04 6.12 (0.146, 0.045) 265 Comparative Example 4 HT-2 2-3 4.06 6.01 (0.145, 0.045) 275 Comparative Example 5 HT-3 2-1 4.15 6.13 (0.146, 0.046) 280 Comparative Example 6 HT-3 2-2 4.17 6.17 (0.147, 0.047) 285 Comparative Example 7 HT-3 2-3 4.19 6.15 (0.145, 0.047) 275 Comparative Example 8 1-1 EB-2 3.98 6.38 (0.145, 0.046) 210 Comparative Example 9 1-2 EB-2 3.97 6.42 (0.146, 0.045) 230 Comparative Example 10 1-3 EB-2 3.92 6.34 (0.145, 0.047) 225 Comparative Example 11 1-1 EB-3 3.92 6.29 (0.146, 0.046) 220 Comparative Example 12 1-2 EB-3 3.93 6.23 (0.146, 0.045) 240 Comparative Example 13 1-3 EB-3 3.94 6.20 (0.145, 0.047) 235 Comparative Example 14 1-1 EB-4 3.88 6.47 (0.146, 0.046) 200 Comparative Example 15 1-2 EB-4 3.87 6.36 (0.146, 0.045) 225 Comparative Example 16 1-3 EB-4 3.86 6.15 (0.145, 0.045) 230 Comparative Example 17 1-1 EB-5 3.95 6.37 (0.147, 0.046) 160 Comparative Example 18 1-2 EB-5 3.92 6.26 (0.146, 0.045) 185 Comparative Example 19 1-3 EB-5 3.93 6.04 (0.146, 0.047) 170

As shown in Table 1, the organic light emitting device of the embodiment in which the compound represented by Formula 1 is used as a hole transport layer material and the compound represented by Formula 2 is used simultaneously as an electron blocking layer material is represented by Formulas 1 and 2 Compared to the organic light emitting diode of Comparative Example employing only one of the indicated compounds or neither, it exhibited superior characteristics in terms of driving voltage, luminous efficiency, and lifetime.

Specifically, in the case of a device using a compound in which Ar1 is a heterocyclic group as shown in Chemical Formula 1 of the present invention, it can be seen that the driving voltage is lower, the efficiency is higher, and the device exhibits the characteristics of a long life than when the compound in which Ar1 is an aryl group is used. . In addition, in the case of a device using a compound having an ortho biphenylene linker as shown in Formula 2 of the present invention, the driving voltage is lower than that of the compound having a para biphenylene linker or a phenylene linker, the efficiency is high, and the long life characteristics can be seen.

Through this, the compound represented by Formula 1 (a structure in which a fluorenyl group and a heterocyclic group (Ar1) are bonded through an amine group at the 2nd position of the fluorene-based core) is used as a hole transport layer material (HTL), Driving voltage and luminous efficiency, especially lifespan, of a blue organic light emitting device made by combining the compound represented by Formula 2 (a monoamine structure in which a biphenylene linker and a carbazole are connected in an ortho direction) with an electron blocking layer material (EBL) of the present invention It can be seen that the properties can be improved.

In general, considering that the luminous efficiency and lifespan characteristics of the organic light emitting device have a trade-off relationship with each other, the organic light emitting device employing the combination of the compounds of the present invention has significantly improved device characteristics compared to the comparative example device. can be seen to indicate

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
5a: first electron blocking layer
5b: second electron blocking layer
5c: third 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 transport and injection layer
9: electron transport layer
9a: first electron transport layer
9b: second electron transport layer
9c: third electron transport layer
10: electron injection 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 (13)

anode;
cathode;
a light emitting layer provided between the anode and the cathode;
a first organic material layer provided between the anode and the light emitting layer;
and a second organic material layer provided between the first organic material layer and the light emitting layer,
The first organic material layer includes a compound represented by Formula 1, and the second organic layer includes a compound represented by Formula 2 below.
[Formula 1]

In Formula 1,
R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; nitrile group; silyl group; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, or a substituted or unsubstituted ring by combining with an adjacent group,
L1 is a direct bond; Or a substituted or unsubstituted arylene group,
Ar1 is a substituted or unsubstituted heterocyclic group,
Ra and Rb are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; nitrile group; silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
a and b are integers from 0 to 7,
when a is 2 or more, two or more Ra are the same as or different from each other, and when b is 2 or more, two or more Rb are the same or different from each other,
[Formula 2]

In Formula 2,
G1 to G3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; nitrile group; silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted ring by combining with an adjacent group,
L2 and L3 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,
Ar2 and Ar3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted aryl group; a substituted or unsubstituted arylalkyl group; a substituted or unsubstituted arylalkenyl group; Or a substituted or unsubstituted heterocyclic group,
g1 is an integer from 0 to 8, and when g1 is 2 or more, G1 of 2 or more are the same as or different from each other,
g2 and g3 are integers from 0 to 4, and when g2 is 2 or more, two or more G2s are the same as or different from each other, and when g3 is 2 or more, two or more G3's are the same as or different from each other. The method according to claim 1,
L1 is a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted anthracenylene group; a substituted or unsubstituted phenanthrenylene group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted phenalene group; or a substituted or unsubstituted pyrene group. The method according to claim 1,
Wherein Chemical Formula 1 is an organic light emitting device represented by the following Chemical Formula 1-1 or 1-2:
[Formula 1-1]

[Formula 1-2]

In Formulas 1-1 and 1-2,
The definitions of R1 to R4, Ra, Rb, L1, a and b are the same as the definitions in Formula 1 above,
X is O; S; or NR;
R, Rc and Rd are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; nitrile group; silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
c is an integer from 0 to 7,
d is an integer from 0 to 8,
When c is 2 or more, two or more Rc are the same as or different from each other, and when d is 2 or more, two or more Rd are the same or different from each other. The method according to claim 1,
Formula 2 is an organic light emitting device represented by any one of Formulas 2-1 to 2-4:
[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

In Formulas 2-1 to 2-4,
The definitions of L2, L3, Ar2, Ar3, G2, G3, g2 and g3 are the same as those in Formula 2 above,
G11 and G12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; nitrile group; silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
g11 is an integer from 0 to 8, and when g11 is 2 or more, 2 or more G11 are the same as or different from each other,
g12 is an integer from 0 to 10, and when g12 is 2 or more, two or more G12s are the same as or different from each other. The method according to claim 1,
The first organic material layer is an organic light emitting device that is provided in contact with the second organic material layer. The method according to claim 1,
The second organic material layer is an organic light emitting device that is provided in contact with the light emitting layer. The method according to claim 1,
The first organic material layer is an organic light emitting device that is a hole injection layer or a hole transport layer. The method according to claim 1,
The second organic material layer is an organic light emitting device that is an electron blocking layer. The organic light-emitting device according to claim 1, wherein the compound represented by Formula 1 is represented by one of the following structural formulas:

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

. The method according to claim 1,
In the organic light emitting device, one or more organic material layers are additionally provided between the anode and the cathode, 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 light emitting layer, an electron transport layer, an electron injection layer. , An organic light-emitting device further comprising at least one of an electron transport and injection layer and a hole blocking layer. The method according to claim 1,
The organic light emitting device further comprises one or more light emitting layers. 13. The method of claim 12,
In the organic light emitting device, one or more organic material layers are additionally provided between the two or more light emitting layers, and the organic material layers include a hole transport layer, a hole injection layer, a hole transport and injection layer, an electron blocking layer, a charge generation layer, a light emitting layer, and an electron transport layer. , The organic light emitting device further comprising at least one of an electron injection layer, an electron transport and injection layer, and a hole blocking layer.

Images