WO2021075852A1 - Compound and organic light emitting element comprising same - Google Patents

Abstract

The present specification relates to a compound of chemical formula 1 and an organic light emitting element comprising same.

Description

Compound and organic light-emitting device comprising the same

This specification claims the benefit of the filing date of the Korean Patent Application No. 10-2019-0129932 filed with the Korean Intellectual Property Office on October 18, 2019, the entire contents of which are incorporated herein.

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

In general, the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy by using an organic material. An organic light-emitting device using the organic light-emitting phenomenon generally has a structure including a first electrode and a second electrode, and an organic material layer therebetween. Here, the organic material layer is often made of a multilayer structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device.For example, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of such an organic light emitting device, when a voltage is applied between the two electrodes, holes are injected into the organic material layer from the first electrode and electrons are injected into the organic material layer from the second electrode, and excitons are formed when the injected holes and electrons meet. , When this exciton falls back to the ground state, it glows.

Development of a new material for the organic light emitting device as described above is continuously required.

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

The present specification provides a compound represented by the following formula (1).

[Formula 1]

In Formula 1,

L1 to L3 are each independently a substituted or unsubstituted arylene group,

R1 and R2 are each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

a to c are each an integer of 0 to 3,

A is represented by the following formula (2),

[Formula 2]

In Chemical Formula 2,

W is CG17G18; SiG17G18; NG19; O; S; Or SO ₂ ,

G1 to G19 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or forms a substituted or unsubstituted ring with a group adjacent to each other,

Any one of G1 to G16 is connected to L3,

When a is 2 or more, L1 is the same as or different from each other,

When b is 2 or more, L2 is the same as or different from each other,

When c is 2 or more, L3 is the same as or different from each other.

In addition, the present application provides a composition for an organic light-emitting device comprising the above-described compound and an alkali metal organic compound.

In addition, the present application is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, and at least one of the organic material layers includes the aforementioned compound.

The organic light-emitting device using the compound according to the exemplary embodiment of the present application is capable of low driving voltage, high luminous efficiency, or long life.

1 shows a structure of an organic light emitting device according to an exemplary embodiment.

2 shows a structure of an organic light emitting device according to another exemplary embodiment.

<Explanation of code>

1: substrate

2: first electrode

3: light-emitting layer

4: second electrode

5: hole injection layer

6: hole transport layer

7: electron injection and transport layer

Hereinafter, the present specification will be described in detail.

The present specification provides a compound represented by Chemical Formula 1.

In the present specification, when a part "includes" a certain component, it 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 positioned "on" another member, this includes not only the case where the member is in contact with the other member, but also the case where another member exists between the two members.

The compound represented by Formula 1 in the present specification is an asymmetric compound having a structure that becomes a fluorene core and a substituent of 1,2,4 triazine. There is a voltage improvement effect due to the formation of a dense film. In particular, structures of P-type or N-type introduced in 1,2,4 triazines control the mobility of electrons to achieve high efficiency, long-lived hole injection, hole transport, hole injection and transport, light emission, electron transport, or electrons. It can be used as an injection material.

Examples of the substituent in the present specification are described below, but are not limited thereto.

The term “substituted” means that the hydrogen atom bonded to the carbon atom of the 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, the position where the substituent can be substituted, and when two or more are substituted , Two or more substituents may be the same or different from each other.

In the present specification, the term “substituted or unsubstituted” refers to deuterium (-D); Halogen group; Nitrile group; Nitro group; Hydroxy group; Amine group; Silyl group; Boron group; Alkoxy group; Alkyl group; Cycloalkyl group; Aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, two or more of the substituents exemplified above are substituted with a connected substituent, or does not have any substituents. For example, the “substituent to 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 to which two phenyl groups are connected.

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

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

In the present specification, the silyl group may be represented by 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 a trimethylsilyl group, a triethylsilyl group, a tert-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, etc. 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 each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. Specifically, the boron group includes a trimethyl boron group, a triethyl boron group, a tert-butyldimethyl boron group, a triphenyl boron group, and a phenyl boron group, but is not limited thereto.

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 alkyl group has 1 to 30 carbon atoms. 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, and the like, but are not limited thereto.

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

Substituents including an alkyl group, an alkoxy group, and other alkyl group moieties described in the present specification include all of the straight chain or branched form.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably 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 cycloalkyl group has 3 to 20 carbon atoms. 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 are not limited thereto.

In the present specification, the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 39 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. The aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, a terphenyl group, or a quarterphenyl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a triphenyl group, a chrysenyl group, a fluorenyl group, a triphenylenyl group, and the like, but is limited thereto. no.

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

등의 스피로플루오렌기,

(9,9-디메틸플루오렌기), 및

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

Spirofluorene groups such as,

(9,9-dimethylfluorene group), and

It may be a substituted fluorenyl group such as (9,9-diphenylfluorene group). However, it is not limited thereto.

In the present specification, the heterocyclic group is a cyclic group including at least one of N, O, P, S, Si, and Se as hetero atoms, and the number of carbons is not particularly limited, but is preferably 2 to 60 carbon atoms. According to an exemplary embodiment, the number of carbon atoms of the heterocyclic group is 2 to 36. Examples of the heterocyclic group include a pyridine group, a pyrrole group, a pyrimidine group, a quinoline group, a pyridazine group, a furan group, a thiophene group, an imidazole group, a pyrazole group, a dibenzofuran group, a dibenzothiophene group, There are carbazole group, benzocarbazole group, benzonaphthofuran group, benzonaphthothiophene group, indenocarbazole group, indolocarbazole group, and the like, but are not limited thereto.

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

In the present specification, the amine group is -NH ₂ ; Alkylamine group; N-alkylarylamine group; Arylamine group; N-arylheteroarylamine group; It may be selected from the group consisting of an N-alkylheteroarylamine group and a heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 9-methyl-anthracenylamine group , Diphenylamine group, N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, N-bi Phenylnaphthylamine group, N-naphthylfluorenylamine group, N-phenylphenanthrenylamine group, N-biphenylphenanthrenylamine group, N-phenylfluorenylamine group, N-phenylterphenylamine Group, N-phenanthrenylfluorenylamine group, N-biphenylfluorenylamine group, and the like, but are not limited thereto.

In the present specification, the N-alkylarylamine group refers to an amine group in which an alkyl group and an aryl group are substituted with N of the amine group.

In the present specification, the N-arylheteroarylamine group refers to an amine group in which an aryl group and a heteroaryl group are substituted with N of the amine group.

In the present specification, the N-alkylheteroarylamine group refers to an amine group in which an alkyl group and a heteroaryl group are substituted with N of the amine group.

In the present specification, an alkylamine group; N-alkylarylamine group; Arylamine group; N-arylheteroarylamine group; The alkyl group, aryl group, and heteroaryl group in the N-alkylheteroarylamine group and the heteroarylamine group are the same as those of the aforementioned alkyl group, aryl group, and heteroaryl group, respectively.

In the present specification, the "adjacent" group means a substituent substituted on an atom directly connected to the atom in which the corresponding substituent is substituted, a substituent located three-dimensionally closest to the corresponding substituent, or another substituent substituted on the atom where the corresponding substituent is substituted. I can. For example, two substituents substituted at an ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as "adjacent" groups to each other.

In the present specification, in a substituted or unsubstituted ring formed by bonding with adjacent groups to each other, "ring" is a hydrocarbon ring; Or a hetero ring.

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

Except that the hetero ring is divalent, the description of the heterocyclic group may be applied.

According to an exemplary embodiment of the present specification, L1 to L3 are each independently a substituted or unsubstituted arylene group.

According to an exemplary embodiment of the present specification, L1 to L3 are each independently a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L1 to L3 are each independently a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, L1 to L3 are each independently a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, L1 to L3 are each independently 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 to L3 are each independently a direct bond; A phenylene group in which a phenyl group or a phenyl group is substituted or unsubstituted with a substituted or unsubstituted dibenzothiophene group; Or a phenyl group or a phenyl group is a substituted or unsubstituted biphenylene group with a substituted or unsubstituted dibenzothiophene group.

According to an exemplary embodiment of the present specification, a to c are integers of 0 to 3, respectively.

According to an exemplary embodiment of the present specification, when a is 2 or more, L1 is the same as or different from each other.

According to an exemplary embodiment of the present specification, when b is 2 or more, L2 is the same as or different from each other.

According to an exemplary embodiment of the present specification, when c is 2 or more, L3 is the same as or different from each other.

According to an exemplary embodiment of the present specification, a to c are integers of 0 to 2, respectively.

According to an exemplary embodiment of the present specification, when a to c are each 2, the structures in parentheses are the same or different from each other.

According to an exemplary embodiment of the present specification, when a is 2, the two L1s are the same as or different from each other.

According to an exemplary embodiment of the present specification, when b is 2, the two L2s are the same as or different from each other.

According to an exemplary embodiment of the present specification, when c is 2, the two L3s are the same as or different from each other.

According to an exemplary embodiment of the present specification, when a is 0 (L1) _a is a direct bond.

According to an exemplary embodiment of the present specification, when b is 0 (L2) _b is a direct bond.

According to an exemplary embodiment of the present specification, when c is 0 (L3) _c is a direct bond.

According to an exemplary embodiment of the present specification, R1 and R2 are each independently 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, R1 and R2 are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heterocyclic group.

According to an exemplary embodiment of the present specification, R1 and R2 are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted C2 to C20 heterocyclic group.

According to an exemplary embodiment of the present specification, R1 and R2 are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted fluoranthenyl group; A substituted or unsubstituted dibenzothiophenyl group; A substituted or unsubstituted carbazolyl group; A substituted or unsubstituted dibenzofuranyl group; Or a substituted or unsubstituted pyridinyl group.

According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formula 4 or 5.

[Formula 4]

[Formula 5]

In Formula 4 or 5, R1, R2, L1 to L3, and a to c are the same as the definition of Formula 1, and G1 to G16 and W are the same as the definition of Formula 2,

R4 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

d is an integer of 1 to 3,

When d is 2 or 3, R4 is the same as or different from each other.

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

[Formula 2-1]

[Formula 2-2]

In Formulas 2-1 and 2-2,

Y is CG17G18; SiG17G18; NG19; O; S; Or SO ₂ ,

G1 to G19 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

Any one of G1 to G16 is connected to L3,

R5 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

e is an integer from 1 to 4,

When e is 2 or more, R5 is the same as or different from each other.

According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-8.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

[Formula 1-7]

[Formula 1-8]

In Formulas 1-1 to 1-8, R1, R2, L1 to L3, and a to c are the same as the definition of Formula 1, and G1 to G16 and W are the same as the definition of Formula 2,

R4 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

d is an integer of 1 to 3,

When d is 2 or 3, R4 is the same as or different from each other.

According to an exemplary embodiment of the present specification, W and Y are each CG17G18; SiG17G18; NG19; O; S; Or SO ₂ .

According to an exemplary embodiment of the present specification, W and Y are each CG17G18, and G17 and G18 are each independently a substituted or unsubstituted alkyl group.

According to an exemplary embodiment of the present specification, W and Y are each CG17G18, and G17 and G18 are each independently an alkyl group.

According to an exemplary embodiment of the present specification, W and Y are each CG17G18, and G17 and G18 are each independently a methyl group.

According to an exemplary embodiment of the present specification, W and Y are each SiG17G18, and G17 and G18 are each independently a substituted or unsubstituted alkyl group.

According to an exemplary embodiment of the present specification, W and Y are each SiG17G18, and G17 and G18 are each independently an alkyl group.

According to an exemplary embodiment of the present specification, W and Y are each SiG17G18, and G17 and G18 are each independently a methyl group.

According to an exemplary embodiment of the present specification, W is each NG19, and G19 may be bonded to an adjacent group to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present specification, W and Y are each S.

According to an exemplary embodiment of the present specification, W and Y are each O.

According to an exemplary embodiment of the present specification, W and Y are each SO ₂ .

According to an exemplary embodiment of the present specification, any one of G1 to G16 is connected to L3, and the others are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

According to an exemplary embodiment of the present specification, G1 to G19 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or forms a substituted or unsubstituted ring with a group adjacent to each other, and any one of G1 to G16 is connected to L3.

According to an exemplary embodiment of the present specification, any one of G1 to G4 is connected to L3, and the others are 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, any one of G1 to G4 is connected to L3, and the others are each independently hydrogen.

According to an exemplary embodiment of the present specification, any one of G9 to G12 is connected to L3, and the others are 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, any one of G9 to G12 is connected to L3, and the others are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

According to an exemplary embodiment of the present specification, G5 to G19 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or to form a substituted or unsubstituted ring with a group adjacent to each other.

According to an exemplary embodiment of the present specification, G5 to G19 are 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, G5 to G19 are hydrogen.

[0366] According to an exemplary embodiment of the present specification, R4 is 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, R4 is hydrogen.

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

.

.

In addition, the present specification provides a composition for an organic light-emitting device comprising the above-described compound and an alkali metal organic compound.

The alkali metal organic compound refers to an alkali metal complex, wherein the alkali metal refers to a Group 1 metal element excluding hydrogen, for example, lithium (Li), sodium (Na), potassium (K), rubidium (Rb ), cesium (Cs) or francium (Fr). The ligand forming a complex with an alkali metal is not particularly limited as long as it can form a complex with an alkali metal.

The alkali metal organic compound may be a lithium complex, and is preferably LiQ, which will be described later.

In the exemplary embodiment of the present specification, the weight ratio of the compound of Formula 1 and the alkali metal organic compound is 1:9 to 9:1, 2:8 to 8:2, 3:7 to 7:3, or 4:6 to It may be 6:4, preferably 5:5 (1:1).

In addition, the present specification provides an organic light-emitting device including the above-described compound.

In an exemplary embodiment of the present specification, the first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, and at least one of the organic material layers includes the compound.

The organic material layer of the organic light emitting device of the present specification may have a single-layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.

In the exemplary embodiment of the present specification, the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the compound.

In the exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes the compound.

In the exemplary embodiment of the present specification, the organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound.

In the exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, a hole injection layer, and a hole transport layer. It further includes one or two or more layers selected from the group consisting of an electron transport layer, an electron injection layer, an electron blocking layer, and a hole blocking layer.

In the exemplary embodiment of the present application, the organic light emitting device includes a first electrode; A second electrode provided to face the first electrode; And a light emitting layer provided between the first electrode and the second electrode. Two or more organic material layers are provided between the light-emitting layer and the first electrode, or between the light-emitting layer and the second electrode, and at least one of the two or more organic material layers includes the compound. In the exemplary embodiment of the present application, the two or more organic material layers may be selected from the group consisting of an electron transport layer, an electron injection layer, a layer that simultaneously transports electrons and injects electrons, and a hole blocking layer, and the second layer At least one of the group consisting of an electron transport layer, an electron injection layer, a layer that simultaneously transports electrons and injects electrons, and a hole blocking layer includes the compound.

In another exemplary embodiment, the organic light emitting device may be a normal type organic light emitting device in which a first electrode, one or more organic material layers, and a second electrode are sequentially stacked on a substrate.

In another exemplary embodiment, the organic light emitting device may be an inverted type organic light emitting device in which a second electrode, one or more organic material layers, and a first electrode are sequentially stacked on a substrate.

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

(1) Anode/Hole Transport Layer/Light-Emitting Layer/Anode

(2) Anode/Hole Injection Layer/Hole Transport Layer/Light-Emitting Layer/Anode

(3) Anode/Hole Injection Layer/Hole Buffer Layer/Hole Transport Layer/Light-Emitting Layer/Anode

(4) Anode/Hole transport layer/Light-emitting layer/Electron transport layer/Anode

(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 suppression layer/light-emitting layer/electron transport layer/cathode

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

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

(13) Anode/hole injection layer/hole transport layer/electron suppression 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/Anode

(15) Anode/Hole transport layer/Light emitting layer/Hole blocking layer/Electron transport layer/Electron injection layer/Anode

(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/Anode

(18) Anode/hole injection layer/hole transport layer/light-emitting layer/layer that simultaneously injects and transports electrons/cathode

(19) Anode/Hole injection layer/Hole transport layer/Electron suppression layer/Light-emitting layer/Hole blocking layer/Electron transport layer/Electron injection layer/Anode

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

(21) Anode/Hole Injection Layer/Hole Transport Layer/Electron Suppression Layer/Light-Emitting Layer/Hole Blocking Layer/Layer for Simultaneous Electron Injection and Transport/Anode

For example, the structure of an organic light-emitting device according to an exemplary embodiment of the present specification is illustrated in FIGS. 1 and 2.

1 illustrates a structure of an organic light-emitting device in which a substrate 1, a first electrode 2, a light emitting layer 3, and a second electrode 4 are sequentially stacked.

2 shows a substrate 1, a first electrode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron injection and transport layer 7, and a second electrode 4 sequentially. The structure of the stacked organic light emitting device is illustrated. In such a structure, the compound may be included in the electron transport layer 7.

The organic light-emitting device of the present specification may be manufactured by materials and methods known in the art, except that at least one of the organic material layers includes the compound of the present specification, that is, the compound.

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

The organic light-emitting device of the present specification may be manufactured by materials and methods known in the art, except that at least one of the organic material layers includes the compound, that is, the compound represented by Formula 1.

For example, the organic light emitting device of the present specification may be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, a metal or a conductive metal oxide or an alloy thereof is deposited on the substrate to form the first electrode. And forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a second electrode thereon. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a second electrode material, an organic material layer, and a first electrode material on a substrate.

In addition, the compound of Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.

In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing an organic material layer and a first electrode material from a second electrode material on a substrate (International Patent Application Publication No. 2003/012890). However, the manufacturing method is not limited thereto.

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

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

The positive electrode is an electrode for injecting holes, and a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer as the positive electrode material. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.

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

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

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the emission layer. The hole transport material is a material capable of transporting holes from the first electrode or the hole injection layer to the emission layer. This large material is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer including a conjugated portion and a non-conjugated portion, but are not limited thereto.

The emission layer may include a host material and a dopant material.

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

When the emission layer emits red light, the emission dopants include 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), but is not limited thereto. When the emission layer emits green light, a _{phosphor such as Ir(ppy) 3} (fac tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq3 (tris(8-hydroxyquinolino)aluminum) may be used as the emission dopant. However, it is not limited thereto. When the light emitting layer emits blue light, the light emitting dopant is a _{phosphorescent material such as (4,6-F2ppy) 2} Irpic, spiro-DPVBi, spiro-6P, distillbenzene (DSB), distrylarylene (DSA), A fluorescent material such as a PFO-based polymer or a PPV-based polymer may be used, but is not limited thereto.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the emission layer. As an electron transport material, a material capable of receiving electrons from the second electrode and transferring them to the emission layer. This is suitable. Specific examples include Al complex of 8-hydroxyquinoline; Complexes containing Alq3; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials that have a low work function and are followed by an aluminum layer or a silver layer. Specifically, they are cesium, barium, calcium, ytterbium, and samarium, and in each case an aluminum layer or a silver layer follows.

The electron injection layer is a layer that injects electrons from an electrode, has an ability to transport electrons, has an electron injection effect from a second electrode, an excellent electron injection effect for a light emitting layer or a light emitting material, A compound that prevents migration to the hole injection layer and has excellent thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, and their derivatives, metals Complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

The electron injection and transport layer is a layer that injects electrons from the cathode and transports the injected electrons to the emission layer. As the material for forming the electron injection and transport layer, a material having an ability to transport electrons, having an excellent electron injection effect for a light emitting layer or a light emitting material, and having high mobility for electrons is suitable.

The electron injection and transport layer may include the compound of Formula 1 of the present specification. In this case, the electron injection and transport layer may include the compound of Formula 1 alone, or may be used by mixing with an additional material.

In the electron injection and transport layer, the additional material that can be used together with the compound of Formula 1 may be mixed with a material known in the art, but it is preferably an alkali metal organic compound.

The alkali metal organic compound refers to an alkali metal complex, wherein the alkali metal refers to a Group 1 metal element excluding hydrogen, for example, lithium (Li), sodium (Na), potassium (K), rubidium (Rb ), cesium (Cs) or francium (Fr). The ligand forming a complex with an alkali metal is not particularly limited as long as it can form a complex with an alkali metal.

The alkali metal organic compound may be a lithium complex, and is preferably LiQ, which will be described later.

In the electron injection and transport layer, the weight ratio of the compound of Formula 1 and the alkali metal organic compound is 1:9 to 9:1, 2:8 to 8:2, 3:7 to 7:3, or 4:6 to 6: It may be 4, preferably 5:5 (1:1).

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

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

An electron blocking layer may be provided between the hole transport layer and the light emitting layer. Materials known in the art may be used for the electron blocking layer.

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

The compound represented by Chemical Formula 1 of the present specification may have a core structure as shown in the following scheme. Substituents may be bonded by methods known in the art, and the type, position, and number of substituents may be changed according to techniques known in the art.

<Reaction Scheme 1>

In the above reaction scheme, R2, L1 to L3, and a to c are the same as the definition of Formula 1, G5 to G16 are the same as the definition of Formula 2,

R4 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

d is an integer of 1 to 3,

When d is 2 or 3, R4 is the same as or different from each other.

Hereinafter, the present specification will be described in more detail through examples. However, the following examples are for illustrative purposes only and are not intended to limit the present specification.

[Example]

Synthesis Example 1

Compound 1-1 (10.8 g, 30 mmol) and compound 1-2 (8.8 g, 33 mmol) were added to a mixed solvent of 1,4-dioxane (150 mL) and toluene (150 mL). After adding 2M K ₂ CO ₃ (200 mL), palladium acetate (Pd(OAc) ₂ , 0.14 g) and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand , Stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare the compound 1. (12.0 g, yield 71%, MS:[M+H]+= 564)

Synthesis Example 2

Compound 2-1 (13.8 g, 30 mmol) and compound 2-2 (12.9 g, 33 mmol) were added to a mixed solvent of 1,4-dioxane (150 mL) and toluene (150 mL). 2M K ₂ CO ₃ (200 mL), Pd(OAc) ₂ (0.14 g) and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand was added, followed by stirring for 5 hours and Refluxed. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare the compound 2. (15.5 g, yield 75%, MS:[M+H]+= 688)

Synthesis Example 3

Compound 3-1 (14.2 g, 30 mmol) and compound 3-2 (10.7 g, 33 mmol) were added to a mixed solvent of 1,41,4-dioxane (150 mL) and toluene (150 mL). . 2M K ₂ CO ₃ (200 mL), Pd(OAc) ₂ (0.14 g) and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand was added, followed by stirring for 5 hours and Refluxed. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare the compound 3. (14.9g, yield 78%, MS:[M+H]+= 636)

Synthesis Example 4

Compound 4-1 (14.2 g, 30 mmol) and compound 4-2 (9.3 g, 33 mmol) were added to a mixed solvent of 1,4-dioxane (150 mL) and toluene (150 mL). 2M K ₂ CO ₃ (200 mL), Pd(OAc) ₂ (0.14 g) and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand was added, followed by stirring for 5 hours and Refluxed. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare the compound 4. (13.2g, yield 74%, MS:[M+H]+= 595)

Synthesis Example 5

Compound 5-1 (16.0 g, 30 mmol) and compound 5-2 (8.8 g, 33 mmol) were added to a mixed solvent of 1,4-dioxane (150 mL) and toluene (150 mL). 2M K ₂ CO ₃ (200 mL), Pd(OAc) ₂ (0.14 g) and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand was added, followed by stirring for 5 hours and Refluxed. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare the compound 5. (14.4 g, yield 75%, MS: [M+H]+= 639)

Synthesis Example 6

Compound 6-1 (16.0 g, 30 mmol) and compound 6-2 (12.3 g, 33 mmol) were added to a mixed solvent of 1,4-dioxane (150 mL) and toluene (150 mL). 2M K ₂ CO ₃ (200 mL), Pd(OAc) ₂ (0.14 g) and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand was added, followed by stirring for 5 hours and Refluxed. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare the compound 6. (16.8g, yield 75%, MS:[M+H]+= 745)

Synthesis Example 7

Compound 7-1 (14.5 g, 30 mmol) and compound 7-2 (12.2 g, 33 mmol) were added to a mixed solvent of 1,4-dioxane (150 mL) and toluene (150 mL). 2M K ₂ CO ₃ (200 mL), Pd(OAc) ₂ (0.14 g) and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand was added, followed by stirring for 5 hours and Refluxed. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare Compound 7. (16.6g, yield 80%, MS:[M+H]+= 691)

Synthesis Example 8

Compound 8-1 (14.2 g, 30 mmol) and compound 8-2 (11.3 g, 33 mmol) were added to a mixed solvent of 1,4-dioxane (150 mL) and toluene (150 mL). 2M K ₂ CO ₃ (200 mL), Pd(OAc) ₂ (0.14 g) and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand was added, followed by stirring for 5 hours and Refluxed. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare Compound 8. (15.9g, yield 81%, MS:[M+H]+= 656)

Synthesis Example 9

Compound 9-1 (16.5 g, 30 mmol) and compound 9-2 (8.8 g, 33 mmol) were added to a mixed solvent of 1,4-dioxane (150 mL) and toluene (150 mL). 2M K ₂ CO ₃ (200 mL), Pd(OAc) ₂ (0.14 g) and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand was added, followed by stirring for 5 hours and Refluxed. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with ethyl acetate to prepare the compound 9. (14.2 g, yield 72%, MS:[M+H]+= 656)

Example 1

A glass substrate coated with a thin film of ITO (indium tin oxide) having a thickness of 1,000Å was put in distilled water dissolved in a detergent and washed with ultrasonic waves. At this time, a product made by Fischer Co. was used as a detergent, and distilled water secondarily filtered with a filter manufactured by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, it was repeated twice with distilled water to perform ultrasonic cleaning for 10 minutes. 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.

The following compound [HI-A] was thermally vacuum deposited to a thickness of 600Å on the prepared ITO transparent electrode to form a hole injection layer. On the hole injection layer, the following hexaazatriphenylene (HAT) (50Å) and the following compound [HT-A] (600Å) were sequentially vacuum deposited to form a hole transport layer.

Subsequently, the following compounds [BH] and [BD] were vacuum-deposited at a weight ratio of 25:1 to a film thickness of 200 Å on the hole transport layer to form a light emitting layer. Compound 1 and [LiQ] (Lithiumquinolate) were vacuum-deposited at a 1:1 weight ratio on the emission layer to form an electron injection and transport layer with a thickness of 350Å. Lithium fluoride (LiF) in a thickness of 10 Å and aluminum in a thickness of 1,000 Å were sequentially deposited on the electron injection and transport layer to form a negative electrode.

In the above process, the deposition rate of the organic material was maintained at 0.4 ~ 0.9 Å/sec, the deposition rate of lithium fluoride at the cathode was 0.3 Å/sec, and the deposition rate of aluminum was 2 Å/sec. ^{Maintaining -7} torr to 5×10 ^-5 torr, an organic light emitting device was manufactured.

Example 2

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 2 was used instead of Compound 1 in the electron injection and transport layer in Example 1.

Example 3

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 3 was used instead of Compound 1 in the electron injection and transport layer in Example 1.

Example 4

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 4 was used instead of Compound 1 in the electron injection and transport layer in Example 1.

Example 5

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 5 was used instead of Compound 1 in the electron injection and transport layer in Example 1.

Example 6

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 6 was used instead of Compound 1 in the electron injection and transport layer in Example 1.

Example 7

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 7 was used instead of Compound 1 in the electron injection and transport layer in Example 1.

Example 8

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 8 was used instead of Compound 1 in the electron injection and transport layer in Example 1.

Example 9

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 9 was used instead of Compound 1 as the electron injection and transport layer in Example 1 above.

Comparative Example 1

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound ET1 was used instead of Compound 1 in the electron injection and transport layer in Example 1.

Comparative Example 2

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound ET2 was used instead of Compound 1 in the electron injection and transport layer in Example 1.

Comparative Example 3

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound ET3 was used instead of Compound 1 in the electron injection and transport layer in Example 1.

Comparative Example 4

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound ET4 was used instead of Compound 1 in the electron injection and transport layer in Example 1.

As in Experimental Examples 1 to 9 and Comparative Examples 1 to 3, the driving voltage and luminous efficiency were measured at a current density of ^{10 mA/cm 2} for an organic light-emitting device manufactured using each compound as an electron transport material, At a current density of 20mA/cm ² , the time (LT98) to be 98% of the initial luminance was measured.

The results are shown in Table 1 below.

division compound Voltage
(V) Current efficiency
(cd/A) LT98 Experimental Example 1 Compound 1 3.48 4.12 80 Experimental Example 2 Compound 2 3.62 4.32 95 Experimental Example 3 Compound 3 3.71 4.44 70 Experimental Example 4 Compound 4 3.75 4.22 70 Experimental Example 5 Compound 5 3.63 4.21 80 Experimental Example 6 Compound 6 3.83 4.50 95 Experimental Example 7 Compound 7 3.52 4.24 75 Experimental Example 8 Compound 8 3.75 4.15 70 Experimental Example 9 Compound 9 3.81 4.12 80 Comparative Example 1 ET1 4.35 3.10 35 Comparative Example 2 ET2 5.00 3.50 45 Comparative Example 3 ET3 5.11 3.70 30 Comparative Example 4 ET4 4.40 3.32 60

As can be seen from the experimental data in Table 1, it was confirmed that the organic light-emitting device using the compound of Formula 1 according to the present invention exhibited excellent properties in terms of efficiency and lifetime.

Claims (12)

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

In Formula 1, L1 to L3 are each independently a substituted or unsubstituted arylene group, R1 and R2 are each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, a to c are each an integer of 0 to 3, A is represented by the following formula (2), [Formula 2]

In Chemical Formula 2, W is CG17G18; SiG17G18; NG19; O; S; Or SO ₂ , G1 to G19 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or forms a substituted or unsubstituted ring with a group adjacent to each other, Any one of G1 to G16 is connected to L3, When a is 2 or more, L1 is the same as or different from each other, When b is 2 or more, L2 is the same as or different from each other, When c is 2 or more, L3 is the same as or different from each other. The compound of claim 1, wherein the formula 2 is represented by the following formula 2-1 or 2-2: [Formula 2-1]

[Formula 2-2]

In Formulas 2-1 and 2-2, Y is CG17G18; SiG17G18; NG19; O; S; Or SO ₂ , G1 to G19 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, R5 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, e is an integer from 1 to 4, When e is 2 or more, the structures in parentheses are the same or different from each other, Any one of G1 to G16 is connected to L3. The compound of claim 1, wherein Formula 1 is represented by any one of the following Formulas 1-1 to 1-8: [Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

[Formula 1-7]

[Formula 1-8]

In Formulas 1-1 to 1-8, R1, R2, L1 to L3, and a to c are the same as the definition of Formula 1, and G1 to G16 and W are the same as the definition of Formula 2, R4 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, d is an integer of 1 to 3. When d is 2 or 3, R4 is the same as or different from each other. The method according to claim 1, L1 to L3 are each independently a substituted or unsubstituted phenylene group; Or a substituted or unsubstituted biphenylene group. The method according to claim 1, G1 to G16 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group. The compound of claim 1, wherein the compound represented by Formula 1 is selected from the following compounds:

. A composition for an organic light-emitting device comprising the compound according to any one of claims 1 to 6 and an alkali metal organic compound. The composition for an organic light-emitting device according to claim 7, wherein the alkali metal organic compound is a lithium complex. The composition for an organic light-emitting device according to claim 7, wherein the weight ratio of the compound and the alkali metal organic compound is 1:9 to 9:1. A first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, At least one of the organic material layers is an organic light-emitting device comprising the compound according to any one of claims 1 to 6. The method of claim 10, The organic material layer includes a light emitting layer, and further comprises one or two or more layers selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an electron blocking layer, and a hole blocking layer. . The method according to claim 10, wherein the organic material layer further comprises an electron transport layer, an electron injection layer, an electron injection and transport layer or a hole blocking layer, The electron transport layer, the electron injection layer, the electron injection and transport layer, or the hole blocking layer is an organic light-emitting device comprising the compound of Formula 1.

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