CN108884059B

CN108884059B - Compound and organic light-emitting element using same

Info

Publication number: CN108884059B
Application number: CN201780021702.XA
Authority: CN
Inventors: 韩美莲; 李东勋; 许瀞午; 张焚在; 姜敏英; 许东旭; 郑珉祐
Original assignee: LG Chem Ltd
Current assignee: LG Chem Ltd
Priority date: 2016-03-30
Filing date: 2017-03-30
Publication date: 2022-03-18
Anticipated expiration: 2037-03-30
Also published as: JP6750783B2; WO2017171420A1; KR101833669B1; JP2019512499A; CN108884059A; KR20170113397A

Abstract

The present specification provides a compound of chemical formula 1 and an organic light emitting device including the same.

Description

Compound and organic light-emitting element using same

Technical Field

The present specification relates to an organic compound and an organic light-emitting element using the same. The present specification claims priority to korean patent application No. 10-2016-.

Background

In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting element utilizing an organic light emitting phenomenon generally has a structure including an anode and a cathode with an organic layer interposed therebetween. In order to improve the efficiency and stability of the organic light-emitting device, the organic layer is often composed of a multilayer structure composed of different materials, and the multilayer structure may be formed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, or the like. With the structure of such an organic electroluminescent element, if a voltage is applied between both electrodes, holes are injected from the anode into the organic layer, electrons are injected from the cathode into the organic layer, excitons (exiton) are formed when the injected holes and electrons meet, and light is emitted when the excitons are transitioned again to the ground state.

There is a continuing need to develop new materials for the above-described organic light emitting elements.

Disclosure of Invention

The present specification describes a compound and an organic light-emitting element including the same.

One embodiment of the present specification provides a compound represented by the following chemical formula 1.

[ chemical formula 1]

In the above chemical formula 1, at least one of X1 to X3 is N, and the remainder are CR,

r are the same or different from each other and each independently is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 3 to 20 carbon atoms,

ar1, Ar2 and-L- (Y) n are different from each other,

ar1 and Ar2 are different from each other and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 3 to 20 carbon atoms,

l is a directly bonded, substituted or unsubstituted monocyclic or polycyclic 2-to 6-valent aryl group of 6 to 20 carbon atoms or substituted or unsubstituted monocyclic or polycyclic 2-to 6-valent heteroaryl group of 3 to 20 carbon atoms,

y is naphthyl, phenanthryl, dimethylfluorenyl, anthracenyl, triphenylenyl, pyrenyl, tetracenyl, phenanthrenyl, phenanthr,

A perylene group, or a fluoranthene group,

n is an integer of 2 to 5, and a plurality of Y's are the same or different.

In addition, one embodiment of the present specification provides an organic light-emitting element including: the organic light emitting device includes a first electrode, a second electrode provided to face the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers include the compound of chemical formula 1.

The compound described in this specification can be used as a material for an organic layer of an organic light-emitting device. The compound according to at least one embodiment can achieve an improvement in efficiency, a low driving voltage, and/or an improvement in lifetime characteristics in an organic light emitting element. In particular, the compound described in the present specification can be used as a hole injection material, a hole transport material, a hole injection and transport material, a light emitting material, an electron transport material, or an electron injection material, and is preferably used as a material for a light emitting layer, an electron transport layer, or an electron injection layer.

Drawings

Fig. 1 illustrates an example of an organic light-emitting element composed of a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.

Fig. 2 illustrates an example of an organic light-emitting element composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron transport layer 8, and a cathode 4.

Fig. 3 is a mass spectrum of compound 1 according to manufacturing example 1.

Fig. 4 is a mass spectrum of compound 2 according to manufacturing example 2.

Fig. 5 is a mass spectrum of compound 3 according to production example 3.

Fig. 6 is a mass spectrum of compound 4 according to production example 4.

Fig. 7 is a mass spectrum of compound 5 according to manufacturing example 5.

Fig. 8 is a mass spectrum of compound 6 according to production example 6.

Fig. 9 is a mass spectrum of compound 9 according to production example 9.

Fig. 10 is a mass spectrum of compound 10 according to manufacturing example 10.

FIG. 11 is a mass spectrum of Compound 11 according to preparation example 11.

Fig. 12 is a mass spectrum of compound 12 according to production example 12.

Fig. 13 is a mass spectrum of compound 13 according to production example 13.

Fig. 14 is a mass spectrum of compound 16 according to production example 16.

Fig. 15 is a mass spectrum of compound 17 according to production example 17.

Fig. 16 is a mass spectrum of compound 20 according to production example 20.

Fig. 17 is a mass spectrum of compound 22 according to production example 22.

Description of the symbols

1: substrate

2: anode

3: luminescent layer

4: cathode electrode

5: hole injection layer

6: hole transport layer

7: electron transport layer

Detailed Description

The present specification will be described in more detail below.

One embodiment of the present specification provides a compound represented by the above chemical formula 1.

Examples of the above-mentioned substituent are described below, but the present invention is not limited thereto.

The term "substituted or unsubstituted" in the present specification means that the substituent is substituted or unsubstituted with one or more substituents selected from deuterium, a halogen group, a nitrile group, a nitro group, an amino group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, and a heterocyclic group, or with 2 or more substituents among the above-exemplified substituents. For example, "a substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which 2 phenyl groups are linked.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, and is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a 1-methylbutyl group, a 1-ethylbutyl group, a pentyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a hexyl group, a n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a 3, 3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, a n-heptyl group, a 1-methylhexyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, an octyl group, a n-octyl group, a tert-octyl group, a 1-methylheptyl group, a 2-ethylhexyl group, a 2-propylpentyl group, a n-nonyl group, a 2, 2-dimethylheptyl group, a 1-ethylpropyl group, a 1, 1-dimethylpropyl group, an isohexyl group, a 4-methylhexyl group, a, 5-methylhexyl, etc., but is not limited thereto.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms of the above alkenyl group is 2 to 6. Specific examples thereof include, but are not limited to, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadiene, allyl, 1-phenylethen-1-yl, 2-diphenylethen-1-yl, 2-phenyl-2- (naphthalen-1-yl) ethen-1-yl, 2-bis (biphenyl-1-yl) ethen-1-yl, stilbenyl, and styryl.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the number of carbon atoms of the above cycloalkyl group is 3 to 6. Specifically, there may be mentioned, but not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like.

In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto. The polycyclic aromatic group may be a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a perylene group,

And a fluorenyl group, but is not limited thereto.

In the case where the above-mentioned fluorenyl group is substituted, it may be

And the like, but is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group containing at least one of O, N, S, Si and Se as a heteroatom, and the number of carbon atoms is not particularly limited, but the number of carbon atoms is preferably one2 to 60. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,

Azolyl group,

Oxadiazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzobenzoxazinyl

Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl (phenanthroline), isoquinoyl

Oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but is not limited thereto.

In the present specification, the heterocyclic group may be monocyclic or polycyclic, may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and may be selected from the examples of the above-mentioned heteroaryl group.

In the present specification, the fused structure may be a structure in which an aromatic hydrocarbon ring is fused to the substituent. For example, the fused ring of benzimidazole may be

And the like, but is not limited thereto.

In the present specification, the arylene group is a 2-valent group, and the above description of the aryl group can be applied thereto.

In the present specification, the heteroarylene group is a 2-valent group, and in addition to this, the above description of the heterocyclic group can be applied.

In one embodiment of the present specification, X1 is N, and X2 and X3 are CR.

In one embodiment of the present specification, X2 is N, and X1 and X3 are CR.

In one embodiment of the present specification, X1 and X2 are N, and X3 is CR.

In one embodiment of the present specification, X2 and X3 are N, and X1 is CR.

In one embodiment of the present disclosure, X1 to X3 are N.

In one embodiment of the present specification, R is hydrogen or deuterium.

In one embodiment of the present specification, R is hydrogen.

In one embodiment of the present specification, Ar1 and Ar2 are different from each other and each independently represents a substituted or unsubstituted monocyclic or polycyclic aromatic group having 6 to 20 carbon atoms or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 3 to 20 carbon atoms.

In one embodiment of the present specification, Ar1 and Ar2 are different from each other and each independently represents a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, Ar1 and Ar2 are different from each other and each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted dimethylfluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted pyrenyl group.

In one embodiment of the present specification, Ar1 and Ar2 are different from each other and each independently represents a phenyl group, a biphenyl group, a phenanthryl group, a dimethylfluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a naphthyl group, or a pyrenyl group.

In one embodiment of the present specification, Ar1 is a phenyl group, and Ar2 is a biphenyl group, a phenanthryl group, a dimethylfluorenyl group, a dibenzofuranyl group, a dibenzothienyl group, a naphthyl group, or a pyrenyl group.

In one embodiment of the present specification, L is a substituted or unsubstituted monocyclic or polycyclic 2-to 4-valent aryl group having 6 to 20 carbon atoms or a substituted or unsubstituted monocyclic or polycyclic 2-to 4-valent heteroaryl group having 3 to 20 carbon atoms.

In one embodiment of the present specification, L is a substituted or unsubstituted monocyclic or polycyclic, 2-to 4-valent aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, L is a substituted or unsubstituted monocyclic or polycyclic, 3-valent aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, the L is a 2-to 4-valent phenyl group, a 2-to 4-valent biphenyl group, a 2-to 4-valent naphthyl group, a 2-to 4-valent phenanthryl group, a 2-to 4-valent carbazolyl group, a 2-to 4-valent pyridyl group, a 2-to 4-valent pyrimidinyl group, a 2-to 4-valent triazinyl group, a 2-to 4-valent quinolyl group, a 2-to 4-valent dibenzofuranyl group, or a 2-to 4-valent dibenzothiophenyl group.

In one embodiment of the present specification, L is a substituted or unsubstituted 3-valent phenyl group, a substituted or unsubstituted 3-valent biphenyl group, a substituted or unsubstituted 3-valent phenanthryl group, a substituted or unsubstituted 3-valent dimethylfluorenyl group, a substituted or unsubstituted 3-valent dibenzofuranyl group, a substituted or unsubstituted 3-valent dibenzothiophenyl group, a substituted or unsubstituted 3-valent naphthyl group, or a substituted or unsubstituted 3-valent pyrenyl group.

In one embodiment of the present specification, L is a 2-to 4-valent phenyl group, a 2-to 4-valent biphenyl group, a 2-to 4-valent phenanthryl group, a 2-to 4-valent dimethylfluorenyl group, a 2-to 4-valent dibenzofuranyl group, a 2-to 4-valent dibenzothiophenyl group, a 2-to 4-valent naphthyl group, or a 2-to 4-valent pyrenyl group.

In one embodiment of the present specification, L is a 3-valent phenylene group, a 3-valent biphenylene group, a 3-valent phenanthrene group, a 3-valent dimethylfluorenyl group, a 3-valent dibenzofuranyl group, a 3-valent dibenzothiophenyl group, a 3-valent naphthyl group, or a 3-valent pyrenyl group.

In one embodiment of the present specification, L is a 2-to 4-valent phenyl group or a 2-to 4-valent biphenyl group.

In one embodiment of the present specification, L is a 3-valent phenyl group or a 3-valent biphenyl group.

In one embodiment of the present specification, Y is selected from the following structural formulae.

In one embodiment of the present specification, Y is naphthyl or phenanthryl.

In one embodiment of the present specification, the plurality of Y is different.

In one embodiment of the present specification, the plurality of Y is the same.

In one embodiment of the present specification, the compound of chemical formula 1 is any one selected from the following structural formulae.

The compound according to an embodiment of the present application can be produced by a production method described later.

For example, the compound of the above chemical formula 1 may be prepared into a core structure as shown in the following reaction formula 1. The substituents may be combined by a method known in the art, and the kind, position or number of the substituents may be changed according to a technique known in the art.

[ reaction formula 1]

In the above reaction formula 1, the compound of the chemical formula a can be obtained by performing a coupling reaction of the triazine (triazine) compound and the linking group in the form of boric acid (boronic acid) or borate (boronate) using Pd as a catalyst.

Equivalent amounts of bis (pinacolato) diboron (bis (pinacolato) are added to bis

The compound of formula B can be obtained by boronation (borylation) reaction in an alkane solvent (dioxane solvent) with KOAc and Pd as catalysts.

The core structure of chemical formula 1 can be obtained by coupling reaction of the compound of chemical formula B with the compound Y.

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

One embodiment of the present application provides an organic light emitting device, including: the organic light-emitting device includes a first electrode, a second electrode provided so as to face the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contain the compound.

In the present specification, when a member is referred to as being "on" another member, it includes not only a case where the member is in contact with the another member but also a case where the another member is present between the two members.

In the present specification, when a part is referred to as "including" a certain component, unless specifically stated to the contrary, it means that the other component may be further included, and the other component is not excluded.

The organic layer of the organic light-emitting device of the present application may be formed of a single-layer structure or a multilayer structure in which two or more organic layers are stacked. For example, as a typical example of the organic light-emitting element of the present invention, the organic light-emitting element 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 organic layers. However, the structure of the organic light emitting element is not limited thereto, and a smaller number of organic layers may be included.

In one embodiment of the present invention, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound.

In one embodiment of the present invention, the organic 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 one embodiment of the present invention, the organic 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 one embodiment of the present invention, the organic layer includes an electron transport layer, an electron injection layer, or a layer that simultaneously injects or transports electrons, and the electron injection layer, the electron transport layer, or the layer that simultaneously injects and transports electrons includes the compound.

In one embodiment of the present invention, the compound is contained in the electron injection layer, the electron transport layer, or the layer that simultaneously injects and transports electrons, and the electron injection layer, the electron transport layer, or the layer that simultaneously injects and transports electrons may contain an additional compound.

In one embodiment of the present invention, the compound is contained in the electron injection layer, the electron transport layer, or the layer in which electrons are injected and transported simultaneously, and the electron injection layer, the electron transport layer, or the layer in which electrons are injected and transported simultaneously may further contain an N-type dopant.

In one embodiment of the present invention, the compound is contained in the electron injection layer, the electron transport layer, or the layer which performs both electron injection and transport, and the electron injection layer, the electron transport layer, or the layer which performs both electron injection and transport may further contain a metal complex.

In one embodiment of the present invention, the compound is contained in the electron injection layer, the electron transport layer, or the layer which performs both electron injection and transport, and the electron injection layer, the electron transport layer, or the layer which performs both electron injection and transport may further contain a basic metal complex.

In one embodiment of the present invention, the compound is contained in the electron injection layer, the electron transport layer, or the layer that simultaneously injects and transports electrons, and the electron injection layer, the electron transport layer, or the layer that simultaneously injects and transports electrons may further contain 8-hydroxyquinoline lithium.

In one embodiment of the present invention, the compound is contained in the electron injection layer, the electron transport layer, or the layer that simultaneously injects and transports electrons, and the compound of the present invention and 8-hydroxyquinoline lithium may be mixed in a ratio of 1: a weight ratio of 9 to 9:1 inclusive.

In one embodiment of the present invention, the compound is contained in the electron injection layer, the electron transport layer, or the layer that simultaneously injects and transports electrons, and the compound of the present invention and the 8-hydroxyquinoline lithium may be mixed in a ratio of 4: a weight ratio of 6 to 6:4 inclusive.

In one embodiment of the present invention, the compound is contained in the electron injection layer, the electron transport layer, or the layer that simultaneously injects and transports electrons, and the compound of the present invention and 8-hydroxyquinoline lithium are mixed in a ratio of 1:1 by weight inclusive.

In one embodiment of the present application, the organic layer has a thickness of

To

More preferably

To

In one embodiment of the present invention, the organic layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer includes the compound.

In one embodiment of the present application, the organic light emitting device includes: the organic light emitting device includes a first electrode, a second electrode provided so as to face the first electrode, a light emitting layer provided between the first electrode and the second electrode, and 2 or more organic layers provided between the light emitting layer and the first electrode or between the light emitting layer and the second electrode, wherein at least one of the 2 or more organic layers contains the compound.

In one embodiment of the present application, the 2 or more organic layers may be 2 or more layers selected from an electron transport layer, an electron injection layer, a layer that simultaneously transports electrons and injects electrons, and a hole blocking layer.

In one embodiment of the present application, the organic layer includes 2 or more electron transport layers, and at least one of the 2 or more electron transport layers includes the compound. Specifically, in one embodiment of the present specification, the compound may be contained in 1 layer of the 2 or more electron transport layers, or may be contained in each of the 2 or more electron transport layers.

In one embodiment of the present application, when the compound is contained in each of the 2 or more electron transport layers, materials other than the compound may be the same as or different from each other.

In one embodiment of the present invention, the organic layer further includes a hole injection layer or a hole transport layer including a compound containing an arylamino group, a carbazolyl group, or a benzocarbazolyl group, in addition to the organic layer including the compound.

In another embodiment, the organic light-emitting element may be a normal type organic light-emitting element having a structure in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate.

In another embodiment, the organic light emitting element may have an inverted structure in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate.

For example, fig. 1 and 2 show an example of the structure of an organic light-emitting element according to an embodiment of the present application.

Fig. 1 illustrates an example of the structure of an organic light-emitting element in which a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4 are sequentially stacked. In the structure described above, the compound may be contained in the light-emitting layer 3.

Fig. 2 illustrates a structure of an organic light-emitting element in which a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 3, an electron transport layer 7, and a cathode 4 are sequentially stacked. In the above structure, the compound may be contained in one or more of the hole injection layer 5, the hole transport layer 6, the light-emitting layer 3, and the electron transport layer 7.

In the above-described structure, the compound may be contained in one or more of the hole injection layer, the hole transport layer, the light-emitting layer, and the electron transport layer.

The organic light-emitting device of the present application can be manufactured using materials and methods known in the art, except that one or more layers of the organic layer contain the compound of the present application, that is, the above compound.

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

The organic light emitting device of the present application may be manufactured using materials and methods known in the art, except that one or more of the organic layers include the compound described above, i.e., the compound represented by chemical formula 1 described above.

For example, the organic light emitting element of the present application can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. In this case, the following method can be used: a metal, a metal oxide having conductivity, or an alloy thereof is deposited on a substrate by a PVD (physical Vapor Deposition) method such as a sputtering method or an electron beam evaporation method to form an anode, an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed on the anode, and a substance which can be used as a cathode is deposited on the organic layer. In addition to the above-described method, a cathode material, an organic layer, and an anode material may be sequentially deposited on a substrate to manufacture an organic light-emitting element.

In addition, when the compound of chemical formula 1 is used to manufacture an organic light emitting device, the organic layer may be formed not only by a vacuum deposition method but also by a solution coating method. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

In addition to this method, an organic light-emitting element can be manufactured by depositing a cathode material, an organic material layer, and an anode material on a substrate in this order (international patent application publication No. 2003/012890). However, the production method is not limited thereto.

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

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

The anode material is preferably a material having a large work function in order to smoothly inject holes into the organic layer. As specific examples of the anode material which can be used in the present invention, metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), and the like; such as ZnO, Al or SnO₂A combination of a metal such as Sb and an oxide; such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole, and polyaniline, but the present invention is not limited thereto.

The cathode material is preferably a material having a small work function in order to easily inject electrons into the organic layer. As cathode materialFor example, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; such as LiF/Al or LiO₂And a multilayer structure material such as Al, but not limited thereto.

The hole injection layer is a layer for injecting holes from the electrode, and the following compounds are preferable as the hole injection substance: has an ability to transport holes, has a hole injection effect from the anode, has an excellent hole injection effect with respect to the light-emitting layer or the light-emitting material, prevents excitons generated in the light-emitting layer from migrating to the electron injection layer or the electron injection material, and has excellent thin film-forming ability. Preferably, the HOMO (highest occupied molecular orbital) of the hole injecting species is between the work function of the anode species and the HOMO of the surrounding organic layer. Specific examples of the hole injecting substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substances, hexanitrile-hexaazatriphenylene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers.

The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer, and the hole transport material is a material that can receive holes from the anode or the hole injection layer and transport the holes to the light-emitting layer. Specific examples thereof include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers in which a conjugated portion and a non-conjugated portion are present simultaneously.

The light-emitting substance is a substance that can receive holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combine them to emit light in the visible light region, and is preferably a substance having high quantum efficiency with respect to fluorescence or phosphorescence. As a specific example, there is an 8-hydroxyquinoline aluminum complex (Alq)₃) (ii) a A carbazole-based compound; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline metal compounds; benzo (b) is

Azole, benzothiazole and benzimidazole-based compounds; a poly (p-phenylene vinyl) (PPV) polymer; spiro (spiroo) compounds; polyfluorene, rubrene, and the like, but are not limited thereto.

The light emitting layer may include a host material and a dopant material. As the host material, there are aromatic fused ring derivatives, heterocyclic ring-containing compounds, and the like. Specifically, the aromatic condensed ring derivative includes an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound, and the like, and the heterocyclic ring-containing compound includes a dibenzofuran derivative and a ladder-type furan compound

Pyrimidine derivatives, etc., but are not limited thereto.

The electron transporting layer is a layer that receives electrons from the electron injecting layer and transports the electrons to the light emitting layer, and the electron transporting material is a material that can receive electrons from the cathode well and transfer the electrons to the light emitting layer, and a material having a high electron mobility is preferable. Specific examples thereof include Al complexes of 8-hydroxyquinoline and Al complexes containing Alq₃The complex of (3), the organic radical compound, the hydroxyflavone-metal complex, etc., but are not limited thereto. The electron transport layer may be used with any desired cathode material as used in the art. Examples of suitable cathode substances are, in particular, the customary substances having a low work function and accompanied by an aluminum or silver layer. In particular cesium, barium, calcium, ytterbium and samarium, which are accompanied by an aluminum or silver layer.

The electron injection layer is a layer for injecting electrons from the electrode, and is preferably a compound of: has an ability to transport electrons, has an electron injection effect from a cathode, has an excellent electron injection effect for a light-emitting layer or a light-emitting material, prevents excitons generated in the light-emitting layer from migrating to a hole-injecting layer, and is excellent in film-forming properties. Specifically, there are fluorenone, anthraquinone dimethane (Anthraquinodimethane), diphenoquinone, thiopyran dioxide, and,

Azole,

Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, metal complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.

Examples of the metal complex include lithium 8-quinolinolato, zinc bis (8-quinolinolato), copper bis (8-quinolinolato), manganese bis (8-quinolinolato), aluminum tris (2-methyl-8-quinolinolato), and gallium tris (8-quinolinolato), bis (10-hydroxybenzo [ h ] quinoline) beryllium, bis (10-hydroxybenzo [ h ] quinoline) zinc, bis (2-methyl-8-quinoline) gallium chloride, bis (2-methyl-8-quinoline) (o-cresol) gallium, bis (2-methyl-8-quinoline) (1-naphthol) aluminum, bis (2-methyl-8-quinoline) (2-naphthol) gallium, and the like, but are not limited thereto.

The hole blocking layer is a layer that blocks holes from reaching the cathode, and can be formed under the same conditions as the hole injection layer in general. Specifically, there are

An oxadiazole derivative or a triazole derivative, a phenanthroline derivative, BCP, an aluminum complex (aluminum complex), and the like, but the present invention is not limited thereto.

The organic light emitting element according to the present specification may be a top emission type, a bottom emission type, or a bidirectional emission type depending on a material used.

Detailed description of the preferred embodiments

The production of the compound represented by the above chemical formula 1 and the organic light emitting device comprising the same is specifically described in the following examples. However, the following examples are intended to illustrate the present specification, and the scope of the present specification is not limited thereto.

< production example >

< production example 1> Synthesis of Compound 1

1) Synthesis of Compound 1-A

2- ([1,1' -biphenyl ] -4-yl) -4-chloro-6-phenyl-1, 3, 5-triazine (15g,43.6mmol) and (3, 5-dichlorophenyl) boronic acid (9.2g,47.9mmol) were dissolved in 150mL of a tetrahydrofuran solvent under a nitrogen stream, and then an aqueous solution of potassium carbonate (12.1g,87.3mmol) was added thereto, followed by stirring with heating. Pd (PPh3)4(1.5g,1.3mmol) was added under reflux, and the mixture was stirred with heating for 6 hours. After the reaction is finished, cooling the temperature to normal temperature, removing the potassium carbonate solution and filtering. The filtered solid was washed with ethanol, thereby producing compound 1-a (17.8g, yield 90%).

MS[M+H]+＝454

2) Synthesis of Compound 1-B

Compound 1-A (17.8g,39.2mmol) and bis (pinacolato) diboron (10.9g,43.1mmol) were dissolved in 180mL of bis under a nitrogen stream

After the alkyl solvent was added potassium acetate (11.5g,117.5mmol), and the mixture was stirred with heating. Pd (dba)2(0.7g.1.2mmol) and PCy3(0.7g,2.4mmol) were added under reflux, and the mixture was stirred under heating for 8 hours. After the reaction is finished, the temperature is reduced to normal temperature, and then the mixture is filtered once to remove impurities. The filtrate was taken in water, extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, the residue was washed with ethanol to give compound 1-B (21g, yield 84%).

MS[M+H]+＝637

3) Synthesis of Compound 1

Compound 1-B (21g,32.9mmol) and 1-bromonaphthalene (14.3g,69.2mmol) were dissolved in tetrahydrofuran under a nitrogen stream, added as an aqueous solution of potassium carbonate (18.2g,132.8mmol), and stirred with heating. Under reflux, Pd (PPh3)4(1.2g,1.0mmol) as a catalyst was added, and the mixture was stirred under heating for 8 hours. After the reaction is finished, cooling the temperature to normal temperature, removing the potassium carbonate solution and filtering. The filtered solid was washed with ethanol, thereby producing compound 1(18g, yield 85%).

MS[M+H]+＝637

The data for confirming the synthesis of the above compound 1 are shown in FIG. 3.

< production example 2> Synthesis of Compound 2

Compound 1-B (21g,32.9mmol) and 2-bromonaphthalene (14.3g,69.2mmol) were dissolved in tetrahydrofuran under a nitrogen stream, added as an aqueous solution of potassium carbonate (18.2g,132.8mmol), and stirred with heating. Under reflux, Pd (PPh3)4(1.2g,1.0mmol) as a catalyst was added, and the mixture was stirred under heating for 8 hours. After the reaction is finished, cooling the temperature to normal temperature, removing the potassium carbonate solution and filtering. The filtered solid was washed with ethanol, thereby producing compound 2(18g, yield 85%).

MS[M+H]+＝637

The data on the confirmation of the synthesis of the above compound 2 are shown in FIG. 4.

< production example 3> Synthesis of Compound 3

1) Synthesis of Compound 3-A

Compound 3-a was produced by the same method as compound 1-a except that (3-bromo-5-chlorophenyl) boronic acid was used instead of (3, 5-dichlorophenyl) boronic acid.

MS[M+H]+＝498

2) Synthesis of Compound 3-B

Compound 3-A (20g,40.1mmol) and 1-naphthylboronic acid (7.6g,44.1mmol) were dissolved in 1.4-bis under a nitrogen stream

After the addition, potassium phosphate (17.0g,80.2mmol) was added in the form of an aqueous solution, and the mixture was stirred with heating. Under reflux, Pd (PPh3)4(1.4g,1.2mmol) as a catalyst was added, and the mixture was stirred with heating for 8 hours. After the reaction was completed, the temperature was lowered to normal temperature, and then the potassium phosphate solution was removed and filtered. The filtered solid was washed with ethanol, thereby producing compound 3-B (18g, yield 82%).

MS[M+H]+＝546

3) Synthesis of Compound 3

Compound 3 was produced in the same manner as compound 1, except that compound 3-B was used instead of compound 1-B and (4- (1-naphthyl) phenyl) boronic acid was used instead of 1-bromonaphthalene.

MS[M+H]+＝714

The data for confirming the synthesis of the above compound 3 are shown in FIG. 5.

< production example 4> Synthesis of Compound 4

Compound 4 was produced by the same method as compound 3, except that (4- (2-naphthyl) phenyl) boronic acid was used instead of (4- (1-naphthyl) phenyl) boronic acid.

MS[M+H]+＝714

The data for confirming the synthesis of the above compound 4 are shown in FIG. 6.

< production example 5> Synthesis of Compound 5

1) Synthesis of Compound 5-B

Compound 5-B was produced in the same manner as compound 3-B, except that 2-naphthylboronic acid was used instead of 1-naphthylboronic acid.

MS[M+H]+＝546

2) Synthesis of Compound 5

Compound 5 was produced by the same method as compound 3, except that compound 5-B was used instead of compound 3-B and (4- (2-naphthyl) phenyl) boronic acid was used instead of (4- (1-naphthyl) phenyl) boronic acid.

MS[M+H]+＝714

The data on the confirmation of the synthesis of the above compound 5 are shown in FIG. 7.

< production example 6> Synthesis of Compound 6

Compound 6 was produced by the same method as compound 5, except that (4- (1-naphthyl) phenyl) boronic acid was used instead of (4- (2-naphthyl) phenyl) boronic acid.

MS[M+H]+＝714

The data on the confirmation of the synthesis of the above compound 6 are shown in FIG. 8.

< production example 7> Synthesis of Compound 7

Compound 7 was produced in the same manner as compound 1, except that 9-bromophenanthrene was used instead of 1-bromonaphthalene.

MS[M+H]+＝738

< production example 8> Synthesis of Compound 8

1) Synthesis of Compound 8-A

Compound 8-a was produced by the same method as compound 1-a except that 2- ([1,1 '-biphenyl ] -3-yl) -4-chloro-6-phenyl-1, 3, 5-triazine was used instead of 2- ([1,1' -biphenyl ] -4-yl) -4-chloro-6-phenyl-1, 3, 5-triazine.

MS[M+H]+＝454

2) Synthesis of Compound 8-B

Compound 8-B was produced in the same manner as Compound 1-B, except that Compound 8-A was used instead of Compound 1-A.

MS[M+H]+＝638

3) Synthesis of Compound 8

Compound 8 was produced by the same method as compound 7, except that compound 8-B was used instead of compound 1-B.

MS[M+H]+＝738

< production example 9> Synthesis of Compound 9

Compound 9 was produced in the same manner as compound 8, except that 1-bromonaphthalene was used instead of 9-bromophenanthrene.

MS[M+H]+＝638

The data on the confirmation of the synthesis of the above compound 9 are shown in FIG. 9.

< production example 10> Synthesis of Compound 10

Compound 10 was produced in the same manner as compound 8, except that 2-bromonaphthalene was used instead of 9-bromophenanthrene.

MS[M+H]+＝638

The data on the confirmation of the synthesis of the above compound 10 are shown in FIG. 10.

< production example 11> Synthesis of Compound 11

1) Synthesis of Compound 11-A

Compound 11-a was produced by the same method as compound 3-a except that 2- ([1,1 '-biphenyl ] -3-yl) -4-chloro-6-phenyl-1, 3, 5-triazine was used instead of 2- ([1,1' -biphenyl ] -4-yl) -4-chloro-6-phenyl-1, 3, 5-triazine.

MS[M+H]+＝499

2) Synthesis of Compound 11-B

Compound 11-B was produced in the same manner as Compound 3-B, except that Compound 11-A was used instead of 3-A.

MS[M+H]+＝546

3) Synthesis of Compound 11

Compound 11 was produced by the same method as compound 3, except that compound 11-B was used instead of compound 3-B.

MS[M+H]+＝714

The data on the confirmation of the synthesis of the above compound 11 are shown in FIG. 11.

< production example 12> Synthesis of Compound 12

Compound 12 was produced by the same method as compound 4, except that compound 11-B was used instead of compound 3-B.

MS[M+H]+＝714

The data on the confirmation of the synthesis of the above compound 12 are shown in FIG. 12.

< production example 13> Synthesis of Compound 13

1) Synthesis of Compound 13-B

Compound 13-B was produced in the same manner as Compound 5-B, except that Compound 11-A was used instead of Compound 3-A.

MS[M+H]+＝546

2) Synthesis of Compound 13

Compound 13 was produced by the same method as compound 5 except that compound 13-B was used instead of compound 5-B.

MS[M+H]+＝714

The data on the confirmation of the synthesis of the above compound 13 are shown in FIG. 13.

< production example 14> Synthesis of Compound 14

Compound 14 was produced by the same method as compound 13, except that (4- (naphthalen-1-yl) phenyl) boronic acid was used instead of (4- (naphthalen-2-yl) phenyl) boronic acid.

MS[M+H]+＝714

< production example 16> Synthesis of Compound 16

1) Synthesis of Compound 16-A

Compound 16-a was produced in the same manner as compound 1-a except that 2-chloro-4- (dibenzo [ b, d ] furan-1-yl) -6-phenyl-1, 3, 5-triazine was used instead of 2- ([1,1' -biphenyl ] -4-yl) -4-chloro-6-phenyl-1, 3, 5-triazine.

MS[M+H]+＝468

2) Synthesis of Compound 16-B

Compound 16-B was produced in the same manner as Compound 1-B, except that Compound 16-A was used instead of Compound 1-A.

MS[M+H]+＝652

3) Synthesis of Compound 16

Compound 16 was produced by the same method as compound 1, except that compound 16-B was used instead of compound 1-B.

MS[M+H]+＝652

The data on the confirmation of the synthesis of the above compound 16 are shown in FIG. 14.

< production example 17> Synthesis of Compound 17

Compound 17 was produced by the same method as Compound 1, except that Compound 16-B was used instead of Compound 1-B and 2-bromonaphthalene was used instead of 1-bromonaphthalene.

MS[M+H]+＝652

The data on the confirmation of the synthesis of the above compound 17 are shown in FIG. 15.

< production example 18> Synthesis of Compound 18

1) Synthesis of Compound 18-A

Compound 18-a was produced in the same manner as compound 3-a except that 2-chloro-4- (dibenzo [ b, d ] furan-1-yl) -6-phenyl-1, 3, 5-triazine was used instead of 2- ([1,1' -biphenyl ] -4-yl) -4-chloro-6-phenyl-1, 3, 5-triazine.

MS[M+H]+＝512

2) Synthesis of Compound 18-B

Compound 18-B was produced in the same manner as Compound 3-B, except that Compound 18-A was used instead of Compound 3-A.

MS[M+H]+＝560

3) Synthesis of Compound 18

Compound 18 was produced by the same method as compound 3, except that compound 18-B was used instead of compound 3-B.

MS[M+H]+＝728

< production example 19> Synthesis of Compound 19

Compound 19 was produced by the same method as compound 4, except that compound 18-B was used instead of compound 3-B.

MS[M+H]+＝728

< production example 20> Synthesis of Compound 20

1) Synthesis of Compound 20-B

Compound 20-B was produced in the same manner as compound 18-B, except that 2-naphthalene boronic acid was used instead of 1-naphthalene boronic acid.

MS[M+H]+＝560

2) Synthesis of Compound 20

Compound 20 was produced by the same method as compound 5, except that compound 20-B was used instead of compound 5-B.

MS[M+H]+＝728

The data on the confirmation of the synthesis of the above compound 20 are shown in FIG. 16.

< production example 21> Synthesis of Compound 21

Compound 21 was produced in the same manner as compound 20, except that (4- (naphthalen-1-yl) phenyl) boronic acid was used instead of (4- (naphthalen-2-yl) phenyl) boronic acid.

MS[M+H]+＝728

< production example 22> Synthesis of Compound 22

Compound 22 was produced in the same manner as compound 16, except that 9-bromophenanthrene was used instead of 1-bromonaphthalene.

MS[M+H]+＝752

The data on the confirmation of the synthesis of the above compound 22 are shown in FIG. 17.

< production example 23> Synthesis of Compound 23

1) Synthesis of Compound 23-A

Compound 23-a was produced by the same method as compound 1-a except that (2, 5-dichlorophenyl) boronic acid was used instead of (3, 5-dichlorophenyl) boronic acid.

MS[M+H]+＝454

2) Synthesis of Compound 23-B

Compound 23-B was produced in the same manner as Compound 1-B using compound 23-A instead of Compound 1-A.

MS[M+H]+＝638

3) Synthesis of Compound 23

Compound 23 was produced by the same method as compound 1, except that compound 23-B was used instead of compound 1-B.

MS[M+H]+＝638

< preparation example 24> Synthesis of Compound 24

Compound 24 was produced in the same manner as compound 23, except that 2-bromonaphthalene was used instead of 1-bromonaphthalene.

MS[M+H]+＝638

< production example 25> Synthesis of Compound 25

Compound 25 was produced in the same manner as compound 23, except that 9-bromophenanthrene was used instead of 1-bromonaphthalene.

MS[M+H]+＝738

< production example 26> Synthesis of Compound 26

1) Synthesis of Compound 26-A

Compound 26-a was produced by the same method as compound 3-a except that 2-chloro-4- (naphthalen-2-yl) -6-phenyl-1, 3, 5-triazine was used instead of 2- ([1,1' -biphenyl ] -4-yl) -4-chloro-6-phenyl-1, 3, 5-triazine and (2-bromo-4-chlorophenyl) boronic acid was used instead of (3-bromo-5-chlorophenyl) boronic acid.

MS[M+H]+＝472

2) Synthesis of Compound 26-B

Compound 26-B was produced in the same manner as Compound 3-B, except that Compound 26-A was used instead of Compound 3-A.

MS[M+H]+＝520

3) Synthesis of Compound 26

Compound 26 was produced in the same manner as compound 3, except that compound 26-B was used instead of compound 3-B and (4- (phenanthren-9-yl) phenyl) boronic acid was used instead of (4- (naphthalen-1-yl) phenyl) boronic acid.

MS[M+H]+＝738

< example >

Example 1

Will be provided with

The glass substrate coated with ITO (indium tin oxide) is put in distilled water in which a detergent is dissolved, and washed by ultrasonic waves. At this time, the detergent was prepared by Fischer Co, and the distilled water was filtered twice by a Filter (Filter) manufactured by Millipore Co. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the completion of the distilled water washing, the mixture was ultrasonically washed with solvents of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transported to a vacuum evaporator.

On the ITO transparent electrode thus prepared

Thermal vacuum deposition of the following Compound [ HI-A ] in thickness]And a hole injection layer is formed. On the above-mentioned hole injection layer successively

The following chemical formula of h mutexaazatriphenylene (HAT) and the following compound [ HT-A ] are vacuum evaporated]

Thereby forming a hole transport layer.

Next, on the hole transport layer, the following compound [ BH ] was vacuum-evaporated at a weight ratio of 25:1]And [ BD ]]To thereby be in film thickness

Forming a light emitting layer. On the light emitting layer, the compound 1 and [ LiQ ] were vacuum-deposited at a weight ratio of 1:1](8-hydroxyquinoline lithium), to obtain

The electron injection and transport layer is formed with a thickness of (1). Sequentially adding lithium fluoride (LiF) on the electron injection and transport layer

Thickness of aluminum and

the thickness is evaporated to form a cathode.

In the above process, the evaporation speed of the organic material is maintained

Sec, maintenance of lithium fluoride at the cathode

Evaporation Rate,/sec, aluminum maintenance

A vapor deposition rate of/sec, and a degree of vacuum maintained at 1X 10 during vapor deposition^-7To 5X 10^-8torr to thereby fabricate an organic light emitting element.

Example 2

An organic light-emitting element was produced in the same manner as in example 1, except that compound 2 was used instead of compound 1 in example 1.

Example 3

An organic light-emitting element was produced in the same manner as in example 1, except that compound 3 was used instead of compound 1 in example 1.

Example 4

An organic light-emitting element was produced in the same manner as in example 1, except that compound 4 was used instead of compound 1 in example 1.

Example 5

An organic light-emitting element was produced in the same manner as in example 1, except that compound 5 was used instead of compound 1 in example 1.

Example 6

An organic light-emitting element was produced in the same manner as in example 1, except that compound 6 was used instead of compound 1 in example 1.

Example 7

An organic light-emitting element was produced in the same manner as in example 1, except that compound 7 was used instead of compound 1 in example 1.

Example 8

An organic light-emitting element was produced in the same manner as in example 1, except that compound 8 was used instead of compound 1 in example 1.

Example 9

An organic light-emitting element was produced in the same manner as in example 1, except that compound 9 was used instead of compound 1 in example 1.

Example 10

An organic light-emitting element was produced in the same manner as in example 1, except that compound 10 was used instead of compound 1 in example 1.

Example 11

An organic light-emitting element was produced in the same manner as in example 1, except that compound 11 was used instead of compound 1 in example 1.

Example 12

An organic light-emitting element was produced in the same manner as in example 1, except that compound 12 was used instead of compound 1 in example 1.

Example 13

An organic light-emitting element was produced in the same manner as in example 1, except that compound 13 was used instead of compound 1 in example 1.

Example 14

An organic light-emitting element was produced in the same manner as in example 1, except that compound 14 was used instead of compound 1 in example 1.

Example 16

An organic light-emitting element was produced in the same manner as in example 1, except that in example 1, the compound 16 was used instead of the compound 1.

Example 17

An organic light-emitting element was produced in the same manner as in example 1, except that compound 17 was used instead of compound 1 in example 1.

Example 18

An organic light-emitting element was produced in the same manner as in example 1, except that compound 18 was used instead of compound 1 in example 1.

Example 19

An organic light-emitting element was produced in the same manner as in example 1, except that compound 19 was used instead of compound 1 in example 1.

Example 20

An organic light-emitting element was produced in the same manner as in example 1, except that in example 1, the compound 20 was used instead of the compound 1.

Example 21

An organic light-emitting element was produced in the same manner as in example 1, except that in example 1, the compound 21 was used instead of the compound 1.

Example 22

An organic light-emitting element was produced in the same manner as in example 1, except that compound 22 was used instead of compound 1 in example 1.

Example 23

An organic light-emitting element was produced in the same manner as in example 1, except that compound 23 was used instead of compound 1 in example 1.

Example 24

An organic light-emitting element was produced in the same manner as in example 1, except that in example 1, the compound 24 was used instead of the compound 1.

Example 25

An organic light-emitting element was produced in the same manner as in example 1, except that in example 1, the compound 25 was used instead of the compound 1.

Example 26

An organic light-emitting element was produced in the same manner as in example 1, except that in example 1, the compound 26 was used instead of the compound 1.

Comparative example 1

An organic light-emitting element was produced in the same manner as in example 1, except that the following compound ET1 was used instead of compound 1 in example 1.

[ET1]

Comparative example 2

In example 1, an organic light-emitting element was produced in the same manner as in example 1, using the following compound ET2 in place of compound 1.

[ET2]

Comparative example 3

An organic light-emitting element was produced in the same manner as in example 1, except that the following compound ET3 was used instead of compound 1 in example 1.

[ET3]

Comparative example 4

An organic light-emitting element was produced in the same manner as in example 1, except that the following compound ET4 was used instead of compound 1 in example 1.

[ET4]

Comparative example 5

An organic light-emitting element was produced in the same manner as in example 1, except that the following compound ET5 was used instead of compound 1 in example 1.

[ET5]

Comparative example 6

An organic light-emitting element was produced in the same manner as in example 1, except that the following compound ET6 was used instead of compound 1 in example 1.

[ET6]

For the organic light emitting elements of the above examples 1 to 14, 16 to 26 and comparative examples 1 to 6, at 10mA/cm²The driving voltage and the luminous efficiency were measured at a current density of 20mA/cm²The time (LT90) to 90% of the initial luminance was measured at the current density of (1). The results are shown in table 1 below.

[ Table 1]

From the results of table 1 described above, it can be confirmed that the compound represented by chemical formula 1 according to an embodiment of the present specification can be used for an organic layer capable of simultaneous electron injection and electron transport of an organic light emitting element.

In particular, it was confirmed that the compounds ET2 and ET6 of comparative examples 2 and 6 showed higher voltage, lower efficiency, and shorter lifetime than the same compounds of Ar1 and Ar2 of the present invention, and the compounds ET3 and ET4 of comparative examples 3 and 4 were compounds having a substituent not included in the definition of Y of the present invention, and showed higher voltage, lower efficiency, and shorter lifetime than the compounds of examples 1 to 14, and 16 to 26.

Claims

1. An organic light-emitting element comprising: a first electrode, a second electrode provided so as to face the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers include an electron transport layer including a compound represented by the following chemical formula 1 and 8-hydroxyquinoline lithium:

chemical formula 1

In the chemical formula 1, at least one of X1 to X3 is N, and the rest are CR,

ar1, Ar2 and-L- (Y) n are different from each other,

ar1 and Ar2 are different from each other and are each independently phenyl, biphenyl, phenanthryl, dimethylfluorenyl, dibenzofuranyl, dibenzothienyl, naphthyl, or pyrenyl,

l is a 2-to 4-valent phenyl group, a 2-to 4-valent biphenyl group, a 2-to 4-valent naphthyl group, a 2-to 4-valent phenanthryl group, a 2-to 4-valent carbazolyl group, a 2-to 4-valent pyridyl group, a 2-to 4-valent pyrimidinyl group, a 2-to 4-valent triazinyl group, a 2-to 4-valent quinolyl group, a 2-to 4-valent dibenzofuranyl group, or a 2-to 4-valent dibenzothiophenyl group, wherein L is not a 2-valent group,

A perylene group, or a fluoranthene group,

n is an integer of 2 to 5, and a plurality of Y's are the same or different.

2. The organic light-emitting element according to claim 1, wherein the L is a 3-valent phenyl group or a 3-valent biphenyl group.

3. The organic light-emitting element according to claim 1, wherein the plurality of ys are the same.

4. The organic light-emitting element according to claim 1, wherein the plurality of ys are different.

5. The organic light-emitting element according to claim 1, wherein the Y is a naphthyl group or a phenanthryl group.

6. The organic light-emitting element according to claim 1, wherein the compound of chemical formula 1 is any one selected from the following structural formulae: