CN113875034A - Organic light emitting device - Google Patents

Abstract

The present specification provides an organic light emitting device, comprising: a first electrode; a second electrode; a light-emitting layer provided between the first electrode and the second electrode; and a first organic layer disposed between the first electrode and the light emitting layer, the first organic layer including a compound represented by chemical formula 1, the light emitting layer including a compound represented by chemical formula 2.

Description

Organic light emitting device

Technical Field

The present application claims priority of korean patent application No. 10-2019-0086858, filed by the korean patent office at 18.7.2019, the entire contents of which are incorporated herein.

The present description relates to organic light emitting devices.

Background

The organic light emitting device has a structure in which an organic thin film is disposed between 2 electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from the 2 electrodes are combined in the organic thin film to be paired, and then quenched and emitted. The organic thin film may be formed of a single layer or a plurality of layers as necessary.

As a substance used in an organic light-emitting device, a pure organic substance or a complex compound of an organic substance and a metal is mainly used, and may be classified into a hole-injecting substance, a hole-transporting substance, a light-emitting substance, an electron-transporting substance, an electron-injecting substance, and the like according to the application. Here, as the hole injecting substance or the hole transporting substance, an organic substance having a p-type property, that is, an organic substance which is easily oxidized and has an electrochemically stable state at the time of oxidation is mainly used. On the other hand, as the electron injecting substance or the electron transporting substance, an organic substance having an n-type property, that is, an organic substance which is easily reduced and has an electrochemically stable state at the time of reduction is mainly used. The light-emitting layer material is preferably a material having both p-type and n-type properties, that is, a material having a stable form in both an oxidized state and a reduced state, and when holes and electrons are recombined in the light-emitting layer to form generated excitons (exiton), a material having high light-emitting efficiency that converts them into light is preferable.

In order to improve the performance, lifetime, or efficiency of organic light emitting devices, development of materials for organic thin films is continuously required.

(Prior Art document) (patent document 1) Korean patent laid-open publication No. 10-2017-058618

Disclosure of Invention

Technical subject

In this specification, an organic light emitting device having characteristics of a low driving voltage, high efficiency, and long life is described.

Means for solving the problems

An embodiment of the present specification provides an organic light emitting device including:

a first electrode;

a second electrode;

a light-emitting layer provided between the first electrode and the second electrode; and

a first organic material layer disposed between the first electrode and the light-emitting layer,

the first organic layer includes a compound represented by the following chemical formula 1,

the light-emitting layer contains a compound represented by the following chemical formula 2.

[ chemical formula 1]

In the above-described chemical formula 1,

ar1 is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

l1 to L3, which are the same or different from each other, are each independently a direct bond, a substituted or unsubstituted alkylene group, a substituted or unsubstituted arylene group, a substituted or unsubstituted alkoxy group having a valence of 2, a substituted or unsubstituted alkenyl group having a valence of 2, or a substituted or unsubstituted heterocyclic group having a valence of 2,

r1 to R6, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

r1 to r4, which are the same or different from each other, are each independently an integer of 0 to 4,

r1 to r4 are integers of 2 or more, the substituents in parentheses may be the same or different from each other,

[ chemical formula 2]

In the above-described chemical formula 2,

r7 to R11, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

r7 is an integer of 1 to 3,

r8 and r9, which are the same or different from each other, are each independently an integer of 1 to 5,

r10 and r11, which are the same as or different from each other, are each independently an integer of 1 to 4,

when r7 to r11 are integers of 2 or more, the substituents in parentheses may be the same or different from each other.

Effects of the invention

The organic light emitting device of the present invention may obtain an organic light emitting device having a low driving voltage, high efficiency, and/or long life by including the compound represented by chemical formula 1 in the first organic layer, while including the compound represented by chemical formula 2 in the light emitting layer.

Drawings

Fig. 1 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a light-emitting layer 6, and a cathode 10.

Fig. 2 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a light-emitting layer 6, an electron transport layer 8, and a cathode 10.

Fig. 3 shows an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light-emitting layer 6, a hole blocking layer 7, an electron transport layer 8, an electron injection layer 9, and a cathode 10.

[ description of symbols ]

1: substrate

2: anode

3: hole injection layer

4: hole transport layer

5: electron blocking layer

6: luminescent layer

7: hole blocking layer

8: electron transport layer

9: electron injection layer

10: cathode electrode

Detailed Description

The present specification will be described in more detail below.

The organic light emitting device of the present invention includes:

a first electrode;

a second electrode;

a light-emitting layer provided between the first electrode and the second electrode; and

and a first organic layer disposed between the first electrode and the light emitting layer, the first organic layer including a compound represented by chemical formula 1, and the light emitting layer including a compound represented by chemical formula 2.

[ chemical formula 1]

In the above-described chemical formula 1,

ar1 is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

l1 to L3, which are the same or different from each other, are each independently a direct bond, a substituted or unsubstituted alkylene group, a substituted or unsubstituted arylene group, a substituted or unsubstituted alkoxy group having a valence of 2, a substituted or unsubstituted alkenyl group having a valence of 2, or a substituted or unsubstituted heterocyclic group having a valence of 2,

r1 to R6, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

r1 to r4, which are the same or different from each other, are each independently an integer of 0 to 4,

r1 to r4 are integers of 2 or more, the substituents in parentheses may be the same or different from each other,

[ chemical formula 2]

In the above-described chemical formula 2,

r7 to R11, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

r7 is an integer of 1 to 3,

r8 and r9, which are the same or different from each other, are each independently an integer of 1 to 5,

r10 and r11, which are the same as or different from each other, are each independently an integer of 1 to 4,

when r7 to r11 are integers of 2 or more, the substituents in parentheses may be the same or different from each other.

In the present specification, when a part of "includes" a certain component is referred to, unless otherwise stated, it means that the other component may be further included without excluding the other component.

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

In the context of the present specification,

indicates the position of the binding to the chemical formula or compound.

In the present specification, examples of the substituent are described below, but the substituent is not limited thereto.

The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is substituted with another substituent, and the substituted position is not limited as long as the hydrogen atom can be substituted, that is, the substituent can be substituted, and when 2 or more substituents are substituted, 2 or more substituents may be the same as or different from each other.

In the present specification, the term "substituted or unsubstituted" means substituted with 1 or 2 or more substituents selected from deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a silyl group, a boryl group, an alkoxy group, an aryloxy group, an alkyl group, a cycloalkyl group, an aryl group, and a heterocyclic group, or a substituent in which 2 or more substituents among the above-exemplified substituents are linked, or does not have any substituent. 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 term "substituted or unsubstituted" means substituted with 1 or 2 or more substituents selected from deuterium, a halogen group, an amine group, a silyl group, an alkyl group, a cycloalkyl group, an aryl group, and a heterocyclic group, or substituted with a substituent in which 2 or more substituents among the above-exemplified substituents are linked, or does not have any substituent.

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

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

In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the compound may have the following structure, but is not limited thereto.

In the present specification, in the ester group, the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms. Specifically, the compound may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 25. Specifically, the compound may have the following structure, but is not limited thereto.

In the present specification, the silyl group may be represented by-SiY_aY_bY_cThe above-mentioned chemical formula is Y_a、Y_bAnd Y_cMay each be hydrogen, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl. Specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.

In this specification, the boron group may be represented BY-BY_dY_eThe above-mentioned chemical formula is Y_dAnd Y_eMay each be hydrogen, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl. The boron group includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group.

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

In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but the number of carbon atoms is preferably 1 to 20. Specifically, it may be methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, etc., but is not limited thereto.

The alkyl group, the alkoxy group and other substituents containing an alkyl moiety described in the present specification are all included in a linear or branched form.

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 number of carbon atoms of the cycloalkyl group is 3 to 30. 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 are, but not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl.

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. As the monocyclic aryl group, a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group and the like are possible, but not limited theretoIs limited thereto. The polycyclic aromatic group may be a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylene group, a triphenyl group, a perylene group,

Examples of the group include, but are not limited to, a fluorenyl group, a triphenylene group, and the like.

In the present specification, the fluorenyl group may be substituted, and 2 substituents may be combined with each other to form a spiro structure.

When the fluorenyl group is substituted, the compound may be

Isospirofluorene group;

(9, 9-dimethylfluorenyl group) and

and substituted fluorenyl groups such as (9, 9-diphenylfluorenyl) and the like. But is not limited thereto.

In the present specification, the aryl group in the aryloxy group can be applied to the description about the aryl group described above.

In the present specification, the heterocyclic group is a cyclic group containing 1 or more of N, O, P, S, Si and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. Examples of the heterocyclic group include, but are not limited to, pyridyl, pyrrolyl, pyrimidinyl, quinolyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, dibenzofuryl, dibenzothienyl, carbazolyl, benzocarbazolyl, naphthobenzofuryl, benzonaphthothienyl, indenocarbazolyl and the like.

In the present specification, the heteroaryl group is an aromatic group, and the above description of the heterocyclic group can be applied thereto.

In the present specification, in a substituted or unsubstituted ring formed by bonding adjacent groups to each other, "ring" means a hydrocarbon ring or a heterocyclic ring.

The hydrocarbon ring may be aromatic, aliphatic, or a fused ring of aromatic and aliphatic, and may be selected from the cycloalkyl groups and the aryl groups.

In the present specification, the aromatic hydrocarbon ring can be applied to the aryl group.

In the present specification, the description about the above aryl group can be applied to arylene groups other than those having a valence of 2.

In the present specification, the description about the above heteroaryl group can be applied, except that the heteroarylene group is a 2-valent group.

In the present specification, the above heterocyclic group can be applied to the explanation of the heterocyclic group except that the heterocyclic group having a valence of 2 is a 2-valent heterocyclic group.

The following describes chemical formula 1 in detail.

[ chemical formula 1]

In the above-described chemical formula 1,

ar1 is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

l1 to L3, which are the same or different from each other, are each independently a direct bond, a substituted or unsubstituted alkylene group, a substituted or unsubstituted arylene group, a substituted or unsubstituted alkoxy group having a valence of 2, a substituted or unsubstituted alkenyl group having a valence of 2, or a substituted or unsubstituted heterocyclic group having a valence of 2,

r1 to R6, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

r1 to r4, which are the same or different from each other, are each independently an integer of 0 to 4,

r1 to r4 are integers of 2 or more, the substituents in parentheses may be the same or different from each other,

according to one embodiment of the present specification, Ar1 is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

According to an embodiment of the present specification, Ar1 is hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

According to one embodiment of the present specification, Ar1 is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

According to one embodiment of the present specification, Ar1 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

According to one embodiment of the present specification, Ar1 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

According to one embodiment of the present specification, Ar1 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

According to one embodiment of the present specification, Ar1 is a substituted or unsubstituted aryl group having 6 to 15 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms.

According to one embodiment of the present specification, Ar1 is a substituted or unsubstituted aryl group having 6 to 10 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 10 carbon atoms.

According to one embodiment of the present specification, Ar1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

According to one embodiment of the present specification, Ar1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted spirobifluorenyl group.

According to an embodiment of the present specification, Ar1 is phenyl substituted or unsubstituted with one or more substituents selected from deuterium, alkyl, and aryl; naphthyl substituted or unsubstituted with one or more substituents selected from deuterium, alkyl, and aryl; a biphenyl group substituted or unsubstituted with one or more substituents selected from deuterium, an alkyl group and an aryl group; a terphenyl group substituted or unsubstituted with one or more substituents selected from deuterium, an alkyl group and an aryl group; phenanthryl substituted or unsubstituted with one or more substituents selected from deuterium, alkyl, and aryl; a triphenylene group which is substituted or unsubstituted with one or more substituents selected from deuterium, an alkyl group and an aryl group; a fluorenyl group substituted or unsubstituted with one or more substituents selected from deuterium, an alkyl group and an aryl group; or spirobifluorenyl which is unsubstituted or substituted with one or more substituents selected from deuterium, an alkyl group and an aryl group.

According to an embodiment of the present description, Ar1 is phenyl substituted or unsubstituted with deuterium; naphthyl substituted or unsubstituted with deuterium; biphenyl substituted or unsubstituted with deuterium; terphenyl optionally substituted with deuterium; phenanthryl substituted or unsubstituted with deuterium; a triphenylene group substituted or unsubstituted with deuterium; a fluorenyl group which is substituted or unsubstituted with one or more substituents selected from deuterium, a methyl group and a phenyl group; or spirobifluorenyl substituted or unsubstituted by deuterium.

According to one embodiment of the present specification, Ar1 is phenyl substituted or unsubstituted with deuterium, naphthyl, biphenyl substituted or unsubstituted with deuterium, terphenyl, phenanthryl, triphenylene, dimethylfluorenyl, diphenylfluorenyl, or spirobifluorenyl.

In one embodiment of the present specification, Ar1 is represented by any one of the following chemical formulae.

In the above formula, R is hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

the dotted line indicates the binding site with L1.

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

According to an embodiment of the present specification, R is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to an embodiment of the present specification, R is an alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms.

According to an embodiment of the present description, R is methyl or phenyl.

In one embodiment of the present specification, Ar1 is represented by any one of the following chemical formulae.

In the above chemical formula, R is as defined above, and the dotted line indicates the binding site to L1.

According to one embodiment of the present description, Ar1 is phenyl or biphenyl.

According to an embodiment of the present description, Ar1 may be substituted with deuterium.

According to an embodiment of the present specification, L1 to L3, which are the same or different from each other, are each independently a direct bond, a substituted or unsubstituted alkylene group, a substituted or unsubstituted arylene group, a substituted or unsubstituted alkoxy group having a valence of 2, a substituted or unsubstituted alkenyl group having a valence of 2, or a substituted or unsubstituted heterocyclic group having a valence of 2.

According to an embodiment of the present specification, L1 to L3, which are the same or different from each other, are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted 2-valent heterocyclic group.

According to an embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently represents a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 valences and having 2 to 30 carbon atoms.

According to an embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently represents a direct bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 valences and having 2 to 20 carbon atoms.

According to an embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently represents a direct bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 valences and having 2 to 15 carbon atoms.

According to an embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently represents a direct bond, a substituted or unsubstituted arylene group having 6 to 10 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 valences and having 2 to 10 carbon atoms.

According to an embodiment of the present description, L1 to L3, equal to or different from each other, are each independently a direct bond, or a substituted or unsubstituted arylene group.

According to an embodiment of the present specification, L1 to L3 are the same as or different from each other, and each is independently a direct bond, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

According to an embodiment of the present specification, L1 to L3 are the same as or different from each other, and each is independently a direct bond, or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

According to an embodiment of the present specification, L1 to L3 are the same as or different from each other, and each is independently a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted triphenylene group, or a substituted or unsubstituted fluorenylene group.

According to an embodiment of the present description, L1 to L3, equal to or different from each other, are each independently a direct bond; phenylene substituted or unsubstituted with deuterium, alkyl or aryl; naphthylene substituted or unsubstituted with deuterium, alkyl or aryl; biphenylene substituted or unsubstituted with deuterium, alkyl or aryl; terphenylene substituted or unsubstituted with deuterium, alkyl or aryl; phenanthrylene substituted or unsubstituted with deuterium, alkyl or aryl; a triphenylene group substituted or unsubstituted with deuterium, an alkyl group or an aryl group; or a fluorenylidene group substituted or unsubstituted with deuterium, an alkyl group or an aryl group.

According to an embodiment of the present description, L1 to L3, equal to or different from each other, are each independently a direct bond; phenylene substituted or unsubstituted with deuterium, alkyl or aryl; naphthylene substituted or unsubstituted with deuterium, alkyl or aryl; biphenylene substituted or unsubstituted with deuterium, alkyl or aryl; or a fluorenylidene group substituted or unsubstituted with deuterium, an alkyl group or an aryl group.

According to an embodiment of the present specification, L1 to L3, which are the same or different from each other, are each independently a phenylene group, a naphthylene group, a biphenylene group, or a dimethylfluorenylene group, which are directly bonded, substituted with deuterium, or unsubstituted.

According to one embodiment of the present specification, L1, which are the same or different from each other, are each independently a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted triphenylene group, or a substituted or unsubstituted fluorenylene group.

According to one embodiment of the present description, L1, which may be the same or different from each other, are each independently a direct bond; phenylene substituted or unsubstituted with deuterium, alkyl or aryl; naphthylene substituted or unsubstituted with deuterium, alkyl or aryl; biphenylene substituted or unsubstituted with deuterium, alkyl or aryl; terphenylene substituted or unsubstituted with deuterium, alkyl or aryl; phenanthrylene substituted or unsubstituted with deuterium, alkyl or aryl; a triphenylene group substituted or unsubstituted with deuterium, an alkyl group or an aryl group; or a fluorenylidene group substituted or unsubstituted with deuterium, an alkyl group or an aryl group.

According to one embodiment of the present description, L1, which may be the same or different from each other, are each independently a direct bond; phenylene substituted or unsubstituted with deuterium, alkyl or aryl; naphthylene substituted or unsubstituted with deuterium, alkyl or aryl; biphenylene substituted or unsubstituted with deuterium, alkyl or aryl; or a fluorenylidene group substituted or unsubstituted with deuterium, an alkyl group or an aryl group.

According to one embodiment of the present specification, L1, which may be the same or different from each other, are each independently a phenylene group, a naphthylene group, a biphenylene group, or a dimethylfluorenylene group, which may be directly bonded, substituted with deuterium, or unsubstituted.

According to one embodiment of the present specification, L2 is a direct bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

According to one embodiment of the present specification, L2 is phenylene substituted or unsubstituted with deuterium or aryl, or biphenylene substituted or unsubstituted with deuterium or aryl.

According to one embodiment of the present specification, L3 is a direct bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

According to one embodiment of the present specification, L3 is phenylene substituted or unsubstituted with deuterium or aryl, or biphenylene substituted or unsubstituted with deuterium or aryl.

According to an embodiment of the present specification, L2 and L3, which are the same or different from each other, are each independently a direct bond, a phenylene group substituted or unsubstituted with deuterium, or a biphenylene group substituted or unsubstituted with deuterium.

According to an embodiment of the present specification, L2 and L3, equal to or different from each other, are each independently a direct bond, a phenylene group substituted or unsubstituted with deuterium, or a biphenylene group.

According to one embodiment of the present specification, L1 to L3 are directly bonded or represented by any one of the following chemical formulae.

In the above-mentioned chemical formula, the metal oxide,

r 'and R' are the same as or different from each other, and each is independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

the dotted lines indicate the bonding position.

According to an embodiment of the present specification, R' and R "are the same or different from each other, and each is independently a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

According to an embodiment of the present specification, R' and R ″ are the same as or different from each other, and each independently is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to an embodiment of the present specification, R' and R ″ are the same as or different from each other, and each is independently an alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms.

According to an embodiment of the present description, R' and R "are the same or different from each other and are each independently methyl or phenyl.

According to an embodiment of the present disclosure, L1 to L3 are directly bonded or represented by any one of the following chemical formulas.

In the above chemical formula, the dotted line represents the binding site.

According to an embodiment of the present description, L1 to L3 are the same or different from each other, and each is independently a direct bond, a phenylene group, or a biphenylene group.

According to an embodiment of the present specification, L1 to L3 are the same as or different from each other, and each is independently phenylene or biphenylene.

According to an embodiment of the present description, each of L1 to L3 may be substituted with deuterium.

According to an embodiment of the present specification, R1 to R6, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

According to an embodiment of the present description, R1 to R6, equal to or different from each other, are each independently hydrogen, deuterium, or a substituted or unsubstituted aryl group.

According to an embodiment of the present specification, R1 to R6, which are the same or different from each other, are each independently hydrogen, deuterium, or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

According to an embodiment of the present specification, R1 to R6, which are the same or different from each other, are each independently hydrogen, deuterium, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to an embodiment of the present specification, R1 to R6, which are the same or different from each other, are each independently hydrogen, deuterium, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

According to an embodiment of the present specification, R1 to R6, equal to or different from each other, are each independently hydrogen, deuterium, or a substituted or unsubstituted phenyl group.

According to an embodiment of the present description, R1 to R6, equal to or different from each other, are each independently hydrogen, deuterium, or phenyl.

According to an embodiment of the present description, R1 to R4 are hydrogen.

According to an embodiment of the present description, R5 and R6, equal to or different from each other, are each independently hydrogen or phenyl.

According to an embodiment of the present description, R1 to R6 are hydrogen.

According to an embodiment of the present specification, r1 to r4 are the same or different from each other and each independently an integer of 0 to 4, and when r1 to r4 are integers of 2 or more, substituents in parentheses are the same or different from each other.

According to an embodiment of the present description, r1 to r4 are each an integer of 1 to 4.

According to an embodiment of the present description, r1 to r4 are 1.

According to an embodiment of the present description, r1 to r4 are 4.

According to one embodiment of the present specification, the compound represented by the above chemical formula 1 has a structure that is bilaterally symmetrical with respect to the Z1 axis as shown in the following structural formula.

According to one embodiment of the present specification, the compound represented by the above chemical formula 1 has a structure asymmetric to the left and right with respect to the Z1 axis as shown in the following structural formula.

The following describes chemical formula 2 in detail.

[ chemical formula 2]

In the above-described chemical formula 2,

r7 to R11, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

r7 is an integer of 1 to 3,

r8 and r9, which are the same or different from each other, are each independently an integer of 1 to 5,

r10 and r11, which are the same as or different from each other, are each independently an integer of 1 to 4,

when r7 to r11 are integers of 2 or more, the substituents in parentheses may be the same or different from each other.

According to an embodiment of the present specification, R7 to R11, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

According to an embodiment of the present specification, R7 to R11 are the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, 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 heterocyclic group having 2 to 30 carbon atoms.

According to an embodiment of the present specification, R7 to R11 are the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, 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 heterocyclic group having 2 to 20 carbon atoms.

According to an embodiment of the present specification, R7 to R11, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted hexahydrocarbazolyl group.

According to one embodiment of the present description, R7 is hydrogen, deuterium, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

According to one embodiment of the present description, R7 is hydrogen; deuterium; an amino group which is substituted or unsubstituted with a group formed by connecting at least one substituent or at least 2 substituents selected from the group consisting of an alkyl group, a halogen group, a cycloalkyl group and an aryl group; a silyl group which is unsubstituted or substituted with one or more substituents selected from an alkyl group, a halogen group, a cycloalkyl group and an aryl group, or a group in which 2 or more substituents are bonded to each other; an alkyl group which is substituted or unsubstituted with a group formed by connecting at least one substituent or at least 2 substituents selected from the group consisting of an alkyl group, a halogen group, a cycloalkyl group and an aryl group; an aryl group which is substituted or unsubstituted with a group formed by connecting at least one substituent or at least 2 substituents selected from the group consisting of an alkyl group, a halogen group, a cycloalkyl group and an aryl group; or a heterocyclic group which is unsubstituted or substituted with at least one substituent selected from the group consisting of an alkyl group, a halogen group, a cycloalkyl group and an aryl group, or a group in which at least 2 substituents are linked.

According to one embodiment of the present description, R7 is hydrogen; deuterium; an amino group which is substituted or unsubstituted with a group formed by connecting at least one substituent or at least 2 substituents selected from the group consisting of an alkyl group, a halogen group, a cycloalkyl group and an aryl group; a silyl group which is unsubstituted or substituted with one or more substituents selected from an alkyl group, a halogen group, a cycloalkyl group and an aryl group, or a group in which 2 or more substituents are bonded to each other; an alkyl group which is substituted or unsubstituted with a group formed by connecting at least one substituent or at least 2 substituents selected from the group consisting of an alkyl group, a halogen group, a cycloalkyl group and an aryl group; an aryl group which is substituted or unsubstituted with a group formed by connecting at least one substituent or at least 2 substituents selected from the group consisting of an alkyl group, a halogen group, a cycloalkyl group and an aryl group; carbazolyl which is substituted or unsubstituted with a group formed by connecting at least one substituent or at least 2 substituents selected from the group consisting of alkyl, halogen, cycloalkyl and aryl; or a hexahydrocarbazolyl group which is unsubstituted or substituted by a group formed by connecting at least one substituent or at least 2 substituents selected from the group consisting of an alkyl group, a halogen group, a cycloalkyl group and an aryl group.

According to one embodiment of the present description, R7 is hydrogen; deuterium; an alkyl group having 1 to 10 carbon atoms; an amino group which is substituted or unsubstituted with one or more substituents selected from the group consisting of an alkyl group having 1 to 10 carbon atoms, a halogen group, a cycloalkyl group having 3 to 10 carbon atoms and an aryl group having 6 to 20 carbon atoms, or a group in which 2 or more substituents are bonded to each other; a silyl group which is substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms; an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with one or more substituents selected from an alkyl group having 1 to 10 carbon atoms and a silyl group or with 2 or more substituents bonded to each other; or a heterocyclic group which is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms.

According to one embodiment of the present description, R7 is hydrogen; deuterium; a methyl group; a tertiary butyl group; a trimethylsilyl group; an amine group which is unsubstituted or substituted with one or more substituents selected from the group consisting of a methyl group, a tert-butyl group, a fluoro group, a cyclohexyl group and a phenyl group; phenyl substituted or unsubstituted with trimethylsilyl; carbazolyl substituted or unsubstituted with methyl or tert-butyl; or hexahydrocarbazolyl substituted or unsubstituted with methyl.

According to one embodiment of the present description, R7 is hydrogen; a methyl group; a tertiary butyl group; a trimethylsilyl group; an amine group which is unsubstituted or substituted with one or more substituents selected from the group consisting of a methyl group, a tert-butyl group, a fluoro group, a cyclohexyl group and a phenyl group; phenyl substituted or unsubstituted with trimethylsilyl; carbazolyl substituted or unsubstituted with methyl or tert-butyl; or hexahydrocarbazolyl substituted or unsubstituted with methyl.

According to one embodiment of the present description, R7 is hydrogen; a methyl group; a tertiary butyl group; a trimethylsilyl group; an amine group substituted or unsubstituted with a methyl group, a tert-butyl group, or a phenyl group substituted or unsubstituted with a fluoro group; an amino group substituted or unsubstituted with a cyclohexyl group; phenyl substituted or unsubstituted with trimethylsilyl; carbazolyl substituted or unsubstituted with tert-butyl; or hexahydrocarbazolyl substituted or unsubstituted with methyl.

According to an embodiment of the present specification, R7 is represented by any one of the following structural formulae.

In the above-mentioned structural formula, the polymer,

indicating the binding site.

According to an embodiment of the present specification, R7 is represented by any one of the following structural formulae.

In the above-mentioned structural formula, the polymer,

indicating the binding site.

According to one embodiment of the present description, R7 is hydrogen, or an amine group substituted or unsubstituted with a phenyl group substituted or unsubstituted with a tert-butyl group.

According to an embodiment of the present specification, R8 and R9, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

According to an embodiment of the present specification, R8 and R9 are the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

According to an embodiment of the present specification, R8 and R9 are the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

According to an embodiment of the present description, R8 and R9, equal to or different from each other, are each independently hydrogen; an amino group which is substituted or unsubstituted with one or more substituents selected from deuterium, an alkyl group, a halogen group, a silyl group, a cycloalkyl group and an aryl group, or a group in which 2 or more substituents are bonded to each other; a silyl group which is unsubstituted or substituted with one or more substituents selected from deuterium, an alkyl group, a halogen group, a silyl group, a cycloalkyl group and an aryl group, or a group in which 2 or more substituents are bonded to each other; an alkyl group which is substituted or unsubstituted with one or more substituents selected from deuterium, an alkyl group, a halogen group, a silyl group, a cycloalkyl group and an aryl group, or a group in which 2 or more substituents are bonded to each other; carbazolyl group substituted or unsubstituted with one or more substituents selected from deuterium, alkyl group, halogen group, silyl group, cycloalkyl group and aryl group or a group formed by connecting 2 or more substituents; or a pyridyl group which is unsubstituted or substituted with one or more substituents selected from deuterium, an alkyl group, a halogen group, a silyl group, a cycloalkyl group and an aryl group, or a group in which 2 or more substituents are bonded to each other.

According to an embodiment of the present description, R8 and R9, equal to or different from each other, are each independently hydrogen; deuterium: a substituted or unsubstituted alkyl group substituted or unsubstituted with one or more substituents selected from deuterium, an alkyl group, a halogen group, a silyl group, and an aryl group, or a group in which 2 or more substituents are bonded to each other; an amino group which is substituted or unsubstituted with one or more substituents selected from deuterium, an alkyl group, a halogen group, a silyl group, and an aryl group, or a group in which 2 or more substituents are linked; an aryl group which is substituted or unsubstituted with one or more substituents selected from deuterium, an alkyl group, a halogen group, a silyl group, and an aryl group, or a group in which 2 or more substituents are bonded to each other; or a heterocyclic group which is unsubstituted or substituted with one or more substituents selected from deuterium, an alkyl group, a halogen group, a silyl group, and an aryl group, or a group in which 2 or more substituents are bonded to each other.

According to an embodiment of the present description, R8 and R9, equal to or different from each other, are each independently hydrogen; deuterium; an alkyl group having 1 to 10 carbon atoms; an amino group which is substituted or unsubstituted with one or more substituents selected from an alkyl group having 1 to 10 carbon atoms and an aryl group having 6 to 20 carbon atoms, or a group in which 2 or more substituents are bonded to each other; an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with one or more substituents selected from deuterium, an alkyl group having 1 to 10 carbon atoms, a halogen group, and a silyl group, or a group in which 2 or more substituents are bonded to each other; or a heterocyclic group having 2 to 20 carbon atoms which is unsubstituted or substituted with one or more substituents selected from deuterium, an alkyl group having 1 to 10 carbon atoms and an aryl group having 6 to 20 carbon atoms, or a group in which 2 or more substituents are bonded.

According to an embodiment of the present description, R8 and R9, equal to or different from each other, are each independently hydrogen; deuterium; a methyl group; a tertiary butyl group; an amino group substituted or unsubstituted with a phenyl group; a phenyl group which is substituted or unsubstituted with one or more substituents selected from deuterium, a methyl group, a tert-butyl group, a fluoro group and a silyl group, or a group in which 2 or more substituents are linked; or a pyridyl group which is substituted or unsubstituted with one or more substituents selected from deuterium, methyl, tert-butyl or phenyl, or a group in which 2 or more substituents are linked.

According to an embodiment of the present description, R8 and R9, equal to or different from each other, are each independently hydrogen; a methyl group; a tertiary butyl group; a diphenylamino group; by deuterium, methyl, tert-butyl, fluoro, CF₃Or phenyl substituted or unsubstituted with trimethylsilyl; or by methyl, tert-butyl, CD₃Or phenyl substituted or unsubstituted pyridyl.

According to an embodiment of the present specification, R8 and R9, which are the same or different from each other, may each be independently represented by any one of the following structural formulae.

In the above-mentioned structural formula, the polymer,

indicating the binding site.

According to an embodiment of the present specification, R8 and R9, which are the same or different from each other, may each be independently represented by any one of the following structural formulae.

In the above-mentioned structural formula, the polymer,

indicating the binding site.

According to an embodiment of the present description, R8 and R9, equal to or different from each other, are each independently hydrogen or tert-butyl.

According to an embodiment of the present specification, R10 and R11, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

According to an embodiment of the present description, R10 and R11, equal to or different from each other, are each independently hydrogen; deuterium; silyl substituted or unsubstituted with alkyl or aryl; an amine group substituted or unsubstituted with an alkyl group, an arylalkyl group, or an aryl group; alkyl substituted or unsubstituted with alkyl or aryl; aryl substituted or unsubstituted with alkyl or aryl; or a heterocyclic group which is unsubstituted or substituted with an alkyl group or an aryl group.

According to an embodiment of the present description, R10 and R11, equal to or different from each other, are each independently hydrogen; deuterium; silyl substituted or unsubstituted with alkyl or aryl; an amine group substituted or unsubstituted with an alkyl group or an aryl group; alkyl substituted or unsubstituted with alkyl or aryl; aryl substituted or unsubstituted with alkyl or aryl; or a heterocyclic group which is unsubstituted or substituted with an alkyl group or an aryl group.

According to an embodiment of the present description, R10 and R11, equal to or different from each other, are each independently hydrogen; deuterium; a silyl group which is substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms; an amine group which is substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms, an arylalkyl group having 6 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms; an alkyl group having 1 to 10 carbon atoms; an aryl group having 6 to 20 carbon atoms; or a heterocyclic group having 2 to 20 carbon atoms.

According to an embodiment of the present specification, R10 and R11 are the same as or different from each other, and each independently represents hydrogen, deuterium, a silyl group substituted with an alkyl group having 1 to 10 carbon atoms or unsubstituted, an amine group substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 20 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms.

According to an embodiment of the present description, R10 and R11, equal to or different from each other, are each independently hydrogen, methyl, tert-butyl, trimethylsilyl, phenyl, carbazolyl, or an amine group substituted with phenyl.

According to an embodiment of the present description, R10 and R11, equal to or different from each other, are each independently hydrogen, methyl, tert-butyl, trimethylsilyl, phenyl, carbazolyl, or diphenylamino.

According to an embodiment of the present description, if any one of R10 and R11 is a substituted or unsubstituted carbazolyl group or a substituted or unsubstituted amine group, the other is hydrogen.

According to an embodiment of the present specification, R10 and R11, which are the same or different from each other, may each be independently represented by any one of the following structural formulae.

In the above-mentioned structural formula, the polymer,

indicating the binding site.

According to an embodiment of the present specification, R10 and R11, which are the same or different from each other, may each be independently represented by any one of the following structural formulae.

In the above-mentioned structural formula, the polymer,

indicating the binding site.

According to an embodiment of the present description, R10 and R11 are hydrogen or tert-butyl.

According to one embodiment of the present description, r7 is an integer from 1 to 3.

According to one embodiment of the present description, r7 is 1.

According to an embodiment of the present description, r8 and r9 are integers from 1 to 5.

According to an embodiment of the present description, r8 and r9 are integers from 1 to 3.

According to an embodiment of the present description, r10 and r11 are integers from 1 to 4.

According to an embodiment of the present description, r10 and r11 are 1.

According to an embodiment of the present specification, when r7 to r11 are integers of 2 or more, the substituents in parentheses are the same or different from each other.

In one embodiment of the present specification, the chemical formula 2 is represented by the following chemical formula 2-1 or 2-2.

[ chemical formula 2-1]

[ chemical formula 2-2]

In the above chemical formulas 2-1 and 2-2,

r8 to R11 and R7 to R11 are as defined in the above chemical formula 2,

r7' is hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group,

g1 and G2, which may be the same or different from each other, are each independently a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl group, or combine with each other to form a ring.

In one embodiment of the present specification, R7' is hydrogen, deuterium, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

According to an embodiment of the present description, R7' is hydrogen; deuterium; a silyl group which is unsubstituted or substituted with one or more substituents selected from an alkyl group, a halogen group, a cycloalkyl group and an aryl group, or a group in which 2 or more substituents are bonded to each other; an alkyl group which is substituted or unsubstituted with a group formed by connecting at least one substituent or at least 2 substituents selected from the group consisting of an alkyl group, a halogen group, a cycloalkyl group and an aryl group; or an aryl group which is unsubstituted or substituted by a group formed by connecting at least one substituent or at least 2 substituents selected from the group consisting of an alkyl group, a halogen group, a cycloalkyl group and an aryl group.

According to an embodiment of the present description, R7' is hydrogen; deuterium; a silyl group which is unsubstituted or substituted with one or more substituents selected from an alkyl group, a halogen group, a cycloalkyl group and an aryl group, or a group in which 2 or more substituents are bonded to each other; an alkyl group which is substituted or unsubstituted with a group formed by connecting at least one substituent or at least 2 substituents selected from the group consisting of an alkyl group, a halogen group, a cycloalkyl group and an aryl group; or an aryl group which is unsubstituted or substituted by a group formed by connecting at least one substituent or at least 2 substituents selected from the group consisting of an alkyl group, a halogen group, a cycloalkyl group and an aryl group.

According to one embodiment of the present specification, R7' is hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a silyl group substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with one or more substituents selected from an alkyl group having 1 to 10 carbon atoms and a silyl group, or with a group in which 2 or more substituents are bonded.

According to an embodiment of the present description, R7' is hydrogen, deuterium, methyl, tert-butyl, trimethylsilyl, or phenyl substituted or unsubstituted with trimethylsilyl.

According to an embodiment of the present description, R7' is hydrogen, methyl, tert-butyl, trimethylsilyl, or phenyl substituted or unsubstituted with trimethylsilyl.

According to an embodiment of the present description, R7' is hydrogen, methyl, tert-butyl, trimethylsilyl, or phenyl substituted or unsubstituted with trimethylsilyl.

According to an embodiment of the present specification, R7' is represented by any one of the following structural formulae.

In the above-mentioned structural formula, the polymer,

indicating the binding site.

According to an embodiment of the present specification, G1 and G2 are the same as or different from each other, and each independently represents a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 2 to 30 carbon atoms, or a ring having 2 to 30 carbon atoms formed by bonding adjacent groups to each other.

According to an embodiment of the present specification, G1 and G2 are the same as or different from each other, and each independently represents a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted aryl group having 2 to 20 carbon atoms, or a ring having 2 to 20 carbon atoms formed by bonding adjacent groups to each other.

According to an embodiment of the present specification, G1 and G2, which are the same or different from each other, are each independently a cycloalkyl group substituted or unsubstituted with an alkyl group or a halogen group, or an aryl group substituted or unsubstituted with an alkyl group or a halogen group, or combine with each other with adjacent groups to form a carbazole ring substituted or unsubstituted with an alkyl group or a halogen group, or a hexahydrocarbazole ring substituted or unsubstituted with an alkyl group or a halogen group.

According to an embodiment of the present specification, G1 and G2 are the same as or different from each other, and each independently represents a cycloalkyl group having 3 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms or a fluoro group, or combines with adjacent groups to form a carbazole ring which is substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms, or a hexahydrocarbazole ring which is substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms.

According to an embodiment of the present description, G1 and G2, equal to or different from each other, are each independently cyclohexyl; or a phenyl group substituted or unsubstituted by a methyl group, a tert-butyl group or a fluoro group, or a hexahydrocarbazole ring substituted or unsubstituted by a methyl group, in combination with adjacent groups to form a carbazole ring substituted or unsubstituted by a tert-butyl group.

According to an embodiment of the present specification, -N (G1) (G2) is represented by any one of the following structural formulae.

In the above-mentioned structural formula, the polymer,

indicating the binding site.

According to an embodiment of the present specification, -N (G1) (G2) is represented by any one of the following structural formulae.

In the above-mentioned structural formula, the polymer,

indicating the binding site.

In one embodiment of the present specification, the chemical formula 2-1 is represented by the following chemical formula 2-1-1.

[ chemical formula 2-1-1]

In the above chemical formula 2-1-1,

r7', R8 to R11 and R7 to R11 are as defined in the above chemical formula 2-1.

According to an embodiment of the present specification, in chemical formula 2 above, when R8 and R9 are 1, at least one of R8 and R9 is bonded at an ortho (ortho) position of a position where N and phenyl are linked.

According to an embodiment of the present specification, in the above chemical formula 2, when R8 and R9 are 1, R8 and R9 are bonded at the ortho position to the position where N and phenyl are bonded.

According to an embodiment of the present specification, in chemical formula 2 above, when R8 is 2 or more, at least one of 2 or more R8 is bonded to the ortho position of the position where N and phenyl are bonded.

According to an embodiment of the present specification, in chemical formula 2 above, when R9 is 2 or more, at least one of 2 or more R9 is bonded to the ortho position of the position where N and phenyl are bonded.

According to an embodiment of the present specification, the compound represented by the above chemical formula 2 has a structure that is bilaterally symmetrical with respect to the Z2 axis as shown in the following structural formula.

According to an embodiment of the present specification, the compound represented by the above chemical formula 2 has a structure asymmetric to the left and right with respect to the Z2 axis as shown in the following structural formula.

According to one embodiment of the present specification, the compound represented by the above chemical formula 1 is represented by any one of the following structural formulae.

According to an embodiment of the present specification, the compound represented by the above chemical formula 2 is represented by any one of the following structural formulae.

In the present invention, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure as described above. In the present invention, the HOMO and LUMO levels of the compound can also be adjusted by introducing various substituents into the core structure having the above-described structure.

The compounds of chemical formulas 1 and 2 according to the present invention can manufacture a core structure as shown in the following general formulas 1 and 2. The substituents may be combined by a method known in the art, and the kind, position and number of the substituents may be changed according to a technique known in the art.

< general formula 1>

< general formula 2>

The above substituents are defined as in the above chemical formulas 1 and 2.

The organic light emitting device of the present invention may be manufactured using a general method and material for manufacturing an organic light emitting device, in addition to forming a light emitting layer using the compounds of chemical formulas 1 and 2.

The organic layer can be formed by using the above compound not only by a vacuum evaporation method but also by a solution coating method in the production of an organic light-emitting device. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

The organic light emitting device of the present invention may include 1 or more organic layers between the first electrode and the second electrode.

The organic layer of the organic light-emitting device of the present invention may have a single-layer structure, or may have a multilayer structure in which 2 or more organic layers are stacked. For example, the organic light emitting device of the present invention may have a structure including 1 or more of a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron transport and injection layer as an organic layer. However, the structure of the organic light emitting device is not limited thereto, and a smaller or greater number of organic layers may be included.

The organic light emitting device of the present invention includes a light emitting layer, a first organic layer disposed between a first electrode and the light emitting layer including a compound represented by chemical formula 1, and the light emitting layer including a compound represented by chemical formula 2.

According to one example, the first organic layer including the above chemical formula 1 has a thickness of

To

Preferably, it is

To

According to an example, the first organic layer of the organic light emitting device of the present invention may be a hole transport layer or an electron blocking layer.

According to one example, the first organic layer of the organic light emitting device of the present invention includes an electron blocking layer including the compound represented by the above chemical formula 1.

According to one example, the first organic layer of the organic light emitting device of the present invention is an electron blocking layer including the compound represented by the above chemical formula 1.

According to one example, the light emitting layer of the organic light emitting device of the present invention includes a dopant, and the dopant is a compound represented by the above chemical formula 2.

According to one example, the first organic layer of the organic light emitting device of the present invention includes the compound represented by the above chemical formula 1 as a hole transport layer, and the light emitting layer includes the compound represented by the above chemical formula 2 as a dopant of the light emitting layer.

According to one example, the first organic layer of the organic light emitting device of the present invention includes the compound represented by the above chemical formula 1 as an electron blocking layer, and the light emitting layer includes the compound represented by the above chemical formula 2 as a dopant of the light emitting layer.

In another embodiment, the first organic layer may include other organic compounds, metals, or metal compounds in addition to the compound represented by chemical formula 1.

In another embodiment, the light emitting layer may include other organic compounds, metals, or metal compounds in addition to the compound represented by chemical formula 2.

In one embodiment of the present specification, the content of the compound represented by chemical formula 2 is 0.01 to 30 parts by weight, preferably 0.1 to 20 parts by weight, and more preferably 0.5 to 10 parts by weight, based on 100 parts by weight of the compound represented by chemical formula 1. The organic light emitting device satisfying the above weight parts shows excellent characteristics in terms of driving voltage, light emitting efficiency, or life.

In one embodiment of the present specification, the light-emitting layer further includes a compound represented by the following chemical formula H.

[ chemical formula H ]

In the above-mentioned chemical formula H,

l21 to L23, which are identical to or different from one another, are each independently a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,

ar21 to Ar23, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

m is 0 or 1.

In one embodiment of the present specification, when m is 0, hydrogen is bonded to the position-L23-Ar 23.

In one embodiment of the present specification, L21 to L23, which are the same or different from each other, are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.

In one embodiment of the present specification, L21 to L23 are the same as or different from each other, and each independently is a direct bond, a phenylene group, a biphenylene group, a naphthylene group, a 2-valent dibenzofuranyl group, or a 2-valent dibenzothiophenyl group.

In one embodiment of the present specification, Ar21 to Ar23, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, Ar21 to Ar23, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In one embodiment of the present specification, Ar21 to Ar23, which are the same or different from each other, are each independently a substituted or unsubstituted monocyclic to tetracyclic aryl group, or a substituted or unsubstituted monocyclic to tetracyclic heteroaryl group.

In one embodiment of the present specification, Ar21 to Ar23 are the same as or different from each other, and each independently is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted phenalene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted naphthobenzofuryl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted naphthobenzothienyl group.

In one embodiment of the present specification, Ar21 to Ar23 are the same as or different from each other, and each independently represents a phenyl group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms, a biphenyl group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms, a naphthyl group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms, a dibenzofuranyl group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms, a naphthobenzofuranyl group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms, a dibenzothiophenyl group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms, or a naphthobenzothiophenyl group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, the compound represented by the above chemical formula H is any one selected from the following compounds.

An organic light emitting device according to an embodiment of the present specification includes a light emitting layer including the compound represented by the chemical formula 2 as a dopant of the light emitting layer and including the compound represented by the chemical formula H as a host of the light emitting layer.

In one embodiment of the present specification, the compound represented by the above chemical formula 2 is contained in an amount of 0.01 to 30 parts by weight, 0.1 to 20 parts by weight, or 0.5 to 10 parts by weight, based on 100 parts by weight of the compound represented by the above chemical formula H.

In one embodiment of the present specification, the light-emitting layer may further include a host material in addition to the compound represented by the chemical formula H. At this time, furtherThe host material (mixed host compound) to be included includes an aromatic fused ring derivative, a heterocyclic ring-containing compound, and the like. Specifically, as the aromatic condensed ring derivative, there are a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound and the like in addition to an anthracene derivative, and as the heterocycle-containing compound, there are a carbazole derivative, a dibenzofuran derivative, a ladder-type furan compound and the like

The pyrimidine derivative, triazine derivative, and the like may be a mixture of 2 or more kinds thereof, but the present invention is not limited thereto.

The weight ratio of the compound represented by the above chemical formula H to the above mixed host compound is 95:5 to 5:95, more preferably 30:70 to 70: 30.

In one embodiment of the present specification, the light-emitting layer includes 1 or 2 or more compounds represented by the chemical formula H.

In one embodiment of the present specification, the light-emitting layer including the compound represented by the above chemical formula 2 and the compound represented by the above chemical formula H is blue.

An organic light emitting device according to an embodiment of the present specification includes 2 or more light emitting layers, and at least one of the 2 or more light emitting layers includes a compound represented by the above chemical formula 2 and a compound represented by the above chemical formula H. The light emitting layer including the compound represented by the above chemical formula 2 and the compound represented by the above chemical formula H is blue, and the light emitting layer not including the compound represented by the above chemical formula 2 and the compound represented by the above chemical formula H may include a blue, red, or green light emitting compound known in the art.

In one embodiment of the present specification, the organic light-emitting device has a structure in which the first organic layer is provided adjacent to the light-emitting layer.

In the organic light emitting device of the present invention, the organic layer may include a hole blocking layer, and the hole blocking layer may use a material known in the art.

In one embodiment of the present disclosure, 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.

For example, the organic light emitting device may have a stacked structure as shown below, but is not limited thereto.

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

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

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

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

(5) Anode/hole transport layer/luminescent layer/electron transport layer/electron injection layer/cathode

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

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

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

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

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

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

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

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

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

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

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

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

In one embodiment of the present specification, the organic light-emitting device may have a structure (normal type) in which an anode, 1 or more organic layers, and a cathode are sequentially stacked on a substrate.

In one embodiment of the present disclosure, the organic light emitting device may have a reverse structure (inverted type) in which an anode, 1 or more organic layers, and a cathode are sequentially stacked on a substrate.

The structure of the organic light emitting device of the present invention may have the structure shown in fig. 1 to 3, but is not limited thereto.

Fig. 1 illustrates a structure of an organic light emitting device in which an anode 2, a light emitting layer 6, and a cathode 10 are sequentially stacked on a substrate 1. In the structure as described above, the above-described compound may be contained in the above-described light-emitting layer 6.

Fig. 2 illustrates a structure of an organic light-emitting device in which an anode 2, a hole injection layer 3, a hole transport layer 6, a light-emitting layer 6, an electron transport layer 8, and a cathode 10 are sequentially stacked on a substrate 1. In the structure as described above, the above-described compound may be contained in the above-described hole injection layer 3, hole transport layer 6, light emitting layer 6, or electron transport layer 8.

Fig. 3 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light-emitting layer 6, a hole blocking layer 7, an electron transport layer 8, an electron injection layer 9, and a cathode 10. In the structure described above, the above-described compound may be contained in the above-described hole injection layer 3, hole transport layer 4, electron blocking layer 5, light emitting layer 6, hole blocking layer 7, electron transport layer 8, or electron injection layer 9.

For example, the organic light emitting device according to the present invention can be manufactured as follows: the organic el device is manufactured by forming an anode by evaporating metal or a metal oxide having conductivity or an alloy thereof on a substrate by a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation, forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, an electron transport layer, and an electron injection layer on the anode, and then evaporating a substance that can be used as a cathode on the organic layer. In addition to this method, a cathode material, an organic layer, and an anode material may be sequentially deposited on a substrate to manufacture an organic light-emitting device.

The organic layer may further include 1 or more layers selected from a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole transport and injection layer.

The organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, a layer for simultaneously injecting and transporting electrons, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron transport and injection layer, and the like. The organic layer can be produced as a smaller number of layers by a solvent process (solvent process) other than the vapor deposition method, for example, spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer method using various polymer materials.

The anode is an electrode for injecting holes, and a substance having a large work function is generally preferable as an anode substance so that holes can be smoothly injected into the organic layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as Zinc Oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); ZnO-Al or SnO₂Sb and the likeA combination of oxides; 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 is an electrode for injecting electrons, and a substance having a small work function is generally preferable as a cathode substance in order to easily inject electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; LiF/Al or LiO₂And a multilayer structure material such as Al, but not limited thereto.

The hole injection layer is a layer that functions to smoothly inject holes from the anode into the light-emitting layer, and the hole injection substance is a substance that can inject holes from the anode well at a low voltage, and preferably, the HOMO (highest occupied molecular orbital) of the hole injection substance is interposed between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injecting substance include, but are not limited to, metalloporphyrin (porphyrine), 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 thickness of the hole injection layer may be 1 to 150 nm. When the thickness of the hole injection layer is 1nm or more, there is an advantage that the hole injection property can be prevented from being lowered, and when the thickness of the hole injection layer is 150nm or less, there is an advantage that the driving voltage can be prevented from being increased to increase the movement of holes when the thickness of the hole injection layer is too large.

The hole transport layer can function to smoothly transport holes, and the hole transport material is a material that can receive holes from the anode or the hole injection layer and transfer them to the light-emitting layer, and is preferably a material having a high mobility to holes. 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.

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

An electron blocking layer may be disposed between the hole transport layer and the light emitting layer. The electron blocking layer may use the above-mentioned compounds or materials known in the art.

In one embodiment of the present specification, the organic light-emitting device may further include 1 or more light-emitting layers in addition to the light-emitting layer.

The light-emitting layer may emit red, green or blue light, and may be formed of a phosphorescent substance or a fluorescent substance. 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 an 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; poly (p-phenylene vinylene) (PPV) polymers; spiro (spiroo) compounds; polyfluorene, rubrene, and the like, but are not limited thereto.

As a host material of the light-emitting layer, there are aromatic fused ring derivatives, heterocyclic ring-containing compounds, and the like. Specifically, the aromatic condensed ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and the heterocyclic ring-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compounds

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

When the light-emitting layer emits red light, as a light-emitting dopant, piqir (acac) (bis (1-phenylisoquinoline) iridium acetylacetonate, bis (1-phenylisoquinoline) acetylacetylacetylacetylateidiam), PQIr (aca)c) Phosphorescent materials such as bis (1-phenylquinolinato) iridium acetylacetonate, bis (1-phenylquinolinato) iridium, PQIR (tris (1-phenylquinolinato) iridium, tris (1-phenylquinolinato) iridium), PtOEP (platinum octaethylporphyrin), and Alq₃(tris (8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) aluminum), and the like), but is not limited thereto. When the light-emitting layer emits green light, Ir (ppy) can be used as a light-emitting dopant₃Phosphorescent substances such as tris (2-phenylpyridinium) iridium and fac tris (2-phenylpyridinium) iridium, and Alq₃(tris (8-hydroxyquinolinato) aluminum) and the like, but is not limited thereto. When the light-emitting layer emits blue light, (4,6-F2ppy) can be used as the light-emitting dopant₂Examples of the fluorescent substance include phosphorescent substances such as Irpic, and fluorescent substances such as spiro-DPVBi (spiro-DPVBi), spiro-6P (spiro-6P), Distyrylbenzene (DSB), Distyrylarylene (DSA), PFO-based polymers, and PPV-based polymers, but are not limited thereto.

A hole blocking layer may be disposed between the electron transport layer and the light emitting layer, and materials known in the art may be used.

The electron transport layer can play a role in smoothly transporting electrons. The electron transport material is a material that can favorably receive electrons from the cathode and transfer them to the light-emitting layer, and is preferably a material having a high mobility to electrons. Specific examples thereof include Al complexes of 8-hydroxyquinoline and Al complexes containing Alq₃The complex of (a), an organic radical compound, a hydroxyflavone-metal complex, etc., but are not limited thereto. The thickness of the electron transport layer may be 1 to 50 nm. When the thickness of the electron transport layer is 1nm or more, there is an advantage that the electron transport property can be prevented from being lowered, and when the thickness of the electron transport layer is 50nm or less, there is an advantage that the driving voltage can be prevented from being increased to increase the movement of electrons.

The electron injection layer can perform a function of smoothly injecting electrons. As the electron-injecting substance, the following compounds are preferred: has the ability to transport electrons, has the effect of injecting electrons from the cathode, and has excellent electron injection effect for the light-emitting layer or the light-emitting materialA compound which prevents excitons generated in the light-emitting layer from migrating to the hole-injecting layer and which is excellent in thin-film-forming ability. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,

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 prevents holes from reaching the cathode and can be formed under the same conditions as those of the hole injection layer. 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 device according to the present invention may be a top emission type, a bottom emission type, or a bi-directional emission type, depending on the material used.

Modes for carrying out the invention

Hereinafter, in order to specifically explain the present specification, the detailed description will be given by referring to examples. However, the embodiments described in the present specification may be modified into various forms, and the scope of the present application is not to be construed as being limited to the embodiments described in detail below. The embodiments of the present application are provided to more fully explain the present specification to those skilled in the art.

Production example 1: production of Compound 1-1

In a 500ml round bottom flask under nitrogen atmosphere, after completely dissolving the compound N, N-bis (4-bromophenyl) - [1,1' -biphenyl ] -4-amine (9.50g, 19.96mmol) and phenanthren-9-ylboronic acid (9.30g, 41.91mmol) in 240ml of tetrahydrofuran, a 2M aqueous solution of potassium carbonate (120ml) was added, and after adding tetrakis (triphenylphosphine) palladium (0.69g, 0.60mmol), the mixture was stirred with heating for 3 hours. The temperature was cooled to room temperature, the aqueous layer was removed, and the residue was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 250ml of ethyl acetate to obtain compound 1-1(8.46g, 63%).

MS[M+H]⁺＝674

Production example 2: production of Compound 1-2

After completely dissolving the compounds 4 '-bromo-N- (4-bromophenyl) -N-phenyl- [1,1' -biphenyl ] -4-amine (10.50g, 22.06mmol) and phenanthren-9-ylboronic acid (10.28g, 46.32mmol) in 240ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, a 2M aqueous potassium carbonate solution (120ml) was added, and tetrakis (triphenylphosphine) palladium (0.76g, 0.66mmol) was added, followed by stirring with heating for 3 hours. After cooling to room temperature, the aqueous layer was removed and dried over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 220ml of ethyl acetate, whereby Compound 1-2(8.95g, 60%) was produced.

MS[M+H]⁺＝674

Production example 3: production of Compounds 1 to 3

In a 500ml round bottom flask under nitrogen atmosphere, after completely dissolving the compounds N- (3-bromophenyl) -N- (4-bromophenyl) - [1,1' -biphenyl ] -4-amine (10.50g, 22.06mmol) and phenanthren-9-ylboronic acid (10.28g, 46.32mmol) in 240ml of tetrahydrofuran, 2M aqueous potassium carbonate (120ml) was added, and after adding tetrakis (triphenylphosphine) palladium (0.76g, 0.66mmol), stirring was performed with heating for 4 hours. After cooling to room temperature, the aqueous layer was removed and dried over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 210ml of ethyl acetate, whereby compound 1-3(9.24g, 62%) was produced.

MS[M+H]⁺＝674

Production example 4: production of Compound 2-1

1) Synthesis of intermediate A

After 10g (44mmol) of 1-bromo-2, 3-dichlorobenzene was dissolved in 100mL of toluene, diphenylamine (2.1 equiv., 92mmol), sodium tert-butoxide (2.7 equiv., 120mmol), BTP (Bis (tri-tert-butylphosphine) palladium (0), Bis (tri-tert-butylphosphine) palladium (0)) (10 mol%) was added, and the mixture was stirred under reflux for 3 hours, whereby intermediate A (2-chloro-N1, N1, N3, N3-tetraphenylbenzene-1, 3-diamine) was synthesized. The obtained intermediate a was purified by column chromatography.

An intermediate A: 446.15 (C)₃₀H₂₃ClN₂)

Yield 15g (75.8%), purity 99.5%

2) Synthesis of Compound 2-1

10g (22mmol) of intermediate A were dissolved in 100mL of tert-butylbenzene and cooled to-78 ℃. Tert-butyllithium (2.0 eq, 44mmol) was injected and stirred for 6 hours. Injection into BBr₃(2.0 eq, 44mmol), stirred for 1 hour and then warmed to ambient temperature. Diisopropylethylamine (2.0 eq, 44mmol) was slowly added dropwise at ambient temperature and stirred under reflux for 2 hours. The reaction is finishedThereafter, the mixture was washed with an aqueous KOAc solution, and the organic layer was distilled under reduced pressure. The obtained solid was purified by recrystallization to obtain compound 2-1.

Compound 2-1: 420.18 (C)₃₀H₂₁BN₂)

The yield was 7.5g (79.8%) and the purity was 99.9%

Production example 5: production of Compound 2-2

1) Synthesis of intermediate B

Intermediate B was synthesized in the same manner as in the synthesis of intermediate a of production example 4, except that bis (4- (tert-butyl) phenyl) amine was used instead of diphenylamine in production example 4.

2) Synthesis of Compound 2-2

Compound 2-2 was synthesized in the same manner as in the synthesis of compound 2-1 of production example 4, except that intermediate B was used instead of intermediate a in production example 4.

Compound 2-2: 644.43 (C)₄₆H₅₃BN₂)

The yield was 7.2g (75%) and the purity was 99.8%

Production example 6: production of Compound 2-3

1) Synthesis of intermediate C

Intermediate C was synthesized in the same manner as in the synthesis of intermediate a in production example 4, except that bis (4- (tert-butyl) phenyl) amine was used instead of diphenylamine and 1, 5-dibromo-2, 3-dichlorobenzene was used instead of 1-bromo-2, 3-dichlorobenzene in production example 4.

2) Synthesis of Compounds 2-3

Compound 2-3 was synthesized in the same manner as in the synthesis of compound 2-1 of production example 4, except that intermediate C was used instead of intermediate a in production example 4.

Compounds 2-3: 924.18 (C)₆₆H₇₈BN₃)

Yield 6.3g (62%), purity 99.8%

Comparative example 1

Indium Tin Oxide (ITO) and a process for producing the same

The glass substrate coated with a thin film of (3) is put in distilled water in which a detergent is dissolved, and washed by ultrasonic waves. In this case, the detergent used was a product of fisher (Fischer Co.) and the distilled water used was distilled water obtained by twice filtration using 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 resultant was ultrasonically washed with a solvent of isopropyl alcohol, acetone, or 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, the following compound HI-1 and the following compound HI-2 were added in such a manner that the ratio was 98:2 (molar ratio)

The hole injection layer is formed by thermal vacuum deposition.

On the hole injection layer, a compound represented by the following chemical formula HT-1 as a substance for transporting holes

Vacuum evaporation is performed to form a hole transport layer.

Then, on the hole transport layer, the film thickness

The following compound EB-1 was vacuum-deposited to form an electron blocking layer.

Then, on the electron blocking layer, the film thickness

A compound represented by the following chemical formula BH-1 and a compound represented by the following chemical formula BD-1 were vacuum-evaporated at a weight ratio of 25:1 to form a light-emitting layer.

On the light-emitting layer, the thickness of the film

The following compound HB-1 was vacuum-deposited to form a hole-blocking layer.

Next, on the hole-blocking layer, the following compound ET-1 and the following compound LiQ (Lithium Quinolate) were vacuum-evaporated at a weight ratio of 1:1 to form a hole-blocking layer

The thickness of (2) forms an electron transport layer. On the electron transport layer, lithium fluoride (LiF) is sequentially added

Thickness of aluminum and

the electron injection layer and the cathode are formed by vapor deposition.

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 of 2X 10 was maintained during vapor deposition^-7～5×10^-6And supporting to thereby fabricate an organic light emitting device.

The compounds used in comparative example 1 are shown below.

Examples 1 to 9 and comparative examples 2 to 21

An organic light-emitting device was produced in the same manner as in comparative example 1, except that in comparative example 1, the compounds described in table 1 below were used instead of the electron blocking layer compound EB-1 and the dopant compound BD-1, respectively. The compounds used in the above examples and comparative examples are shown below.

Examples of the experiments

The organic light emitting devices manufactured in the above examples and comparative examples were applied with 20mA/cm²At a current of 20mA/cm for the organic light emitting device manufactured as described above²The driving voltage, the luminous efficiency and the color coordinate were measured at a current density of 20mA/cm²The time until the initial luminance reached 95% was measured at the current density of (1) (T95). The results are shown in table 1 below. T95 refers to the time required for the luminance to decrease from the initial luminance (1600 nits) to 95%.

[ Table 1]

As shown in table 1 above, the organic light emitting devices of examples using the compound represented by chemical formula 1 above as an electron blocking layer material while using the compound represented by chemical formula 2 above as a dopant material of a light emitting layer showed excellent characteristics in terms of driving voltage, light emitting efficiency, and lifetime, as compared to the organic light emitting devices of comparative examples 2 to 13 and 16 to 21 using only one of the compounds represented by chemical formulas 1 and 2 above.

It was confirmed that the efficiency and lifetime characteristics of the organic light emitting device according to the embodiment of the present invention using all of the compound represented by the above chemical formula 1 and the compound represented by the above chemical formula 2 were simultaneously improved. In this regard, in consideration of the fact that the light emission efficiency and the life time characteristics of the organic light emitting device have a Trade-off relationship with each other in a general case, it is known that the organic light emitting device employing the combination between the compounds of the present invention shows significantly improved device characteristics as compared with the comparative example device.

Claims (14)

1. An organic light emitting device, comprising:

a first electrode;

a second electrode;

a light emitting layer disposed between the first electrode and the second electrode; and

a first organic layer disposed between the first electrode and the light emitting layer,

the first organic layer includes a compound represented by the following chemical formula 1,

the light emitting layer includes a compound represented by the following chemical formula 2:

chemical formula 1

In the chemical formula 1, the first and second organic solvents,

ar1 is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

l1 to L3, which are the same or different from each other, are each independently a direct bond, a substituted or unsubstituted alkylene group, a substituted or unsubstituted arylene group, a substituted or unsubstituted alkoxy group having a valence of 2, a substituted or unsubstituted alkenyl group having a valence of 2, or a substituted or unsubstituted heterocyclic group having a valence of 2,

r1 to R6, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

r1 to r4, which are the same or different from each other, are each independently an integer of 0 to 4,

r1 to r4 are integers of 2 or more, the substituents in parentheses may be the same or different from each other,

chemical formula 2

In the chemical formula 2,

r7 to R11, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

r7 is an integer of 1 to 3,

r8 and r9, which are the same or different from each other, are each independently an integer of 1 to 5,

r10 and r11, which are the same as or different from each other, are each independently an integer of 1 to 4,

when r7 to r11 are integers of 2 or more, the substituents in parentheses may be the same or different from each other.

2. The organic light-emitting device according to claim 1, wherein Ar1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted spirobifluorenyl group.

3. The organic light-emitting device according to claim 1, wherein the Ar1 is represented by any one of the following chemical formulae:

in the chemical formula, the compound represented by the formula,

r is hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

the dotted line indicates the binding site with L1.

4. The organic light-emitting device according to claim 1, wherein the L1 to L3 are the same as or different from each other, and each is independently a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted triphenylene group, or a substituted or unsubstituted fluorenylene group.

5. The organic light emitting device of claim 1, wherein the L1-L3 are direct bonds or are represented by any one of the following chemical formulas:

in the chemical formula, the compound represented by the formula,

r 'and R' are hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

the dotted lines indicate the bonding position.

6. The organic light emitting device of claim 1, wherein the R1-R4 are hydrogen.

7. The organic light-emitting device according to claim 1, wherein the R7 to R11 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted hexahydrocarbazolyl group.

8. The organic light emitting device according to claim 1, wherein the compound represented by the chemical formula 1 is represented by any one of the following structural formulae:

9. the organic light emitting device according to claim 1, wherein the compound represented by the chemical formula 2 is represented by any one of the following structural formulae:

10. the organic light emitting device according to claim 1, wherein the first organic layer comprises an electron blocking layer comprising the compound represented by chemical formula 1.

11. The organic light emitting device according to claim 1, wherein the light emitting layer comprises a dopant comprising the compound represented by chemical formula 2.

12. The organic light emitting device according to claim 1, wherein the first organic layer comprising the chemical formula 1 has a thickness of

To

13. The organic light-emitting device according to claim 1, wherein the light-emitting layer further comprises a compound represented by the following chemical formula H:

chemical formula H

In the chemical formula H, the compound represented by the formula,

l21 to L23, which are identical to or different from one another, are each independently a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,

ar21 to Ar23, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

m is 0 or 1.

14. The organic light-emitting device according to claim 1, wherein 1 or more organic layers are provided between the first electrode and the second electrode, and the organic layers further comprise 1 or more of a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole transport and injection layer.

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