CN111511733A

CN111511733A - Compound and organic light emitting device including the same

Info

Publication number: CN111511733A
Application number: CN201980006584.4A
Authority: CN
Inventors: 河宰承; 金渊焕; 李成宰; 文贤真
Original assignee: LG Chem Ltd
Current assignee: LG Chem Ltd
Priority date: 2018-04-11
Filing date: 2019-04-11
Publication date: 2020-08-07
Anticipated expiration: 2039-04-11
Also published as: WO2019199068A1; CN111511733B; KR102201553B1; KR20190118980A

Abstract

The present specification relates to a compound represented by chemical formula 1 and an organic light emitting device including the same.

Description

Compound and organic light emitting device including the same

Technical Field

The present invention claims priority of korean patent application No. 10-2018-0042393 filed from korean patent office on 11.04.2018, the entire contents of which are incorporated herein.

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 can 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 use. Here, as the hole injecting substance or the hole transporting substance, an organic substance having p-type properties, 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 is preferably a material having high light emission efficiency in which excitons (exitons) generated by recombination of holes and electrons in the light-emitting layer are formed and converted into light.

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

Disclosure of Invention

Technical subject

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

Means for solving the problems

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

[ chemical formula 1]

In the chemical formula 1, the first and second,

x1 is O or S,

r1 to R6 are each independently hydrogen, deuterium, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amide group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group(s) ((R))

Alkyl thioaxy), substituted or unsubstituted arylthio(s) ((R)

Aryl thio), substituted or unsubstituted alkylsulfonyl(s) ((s)

Alkyl sulfoxy), substituted or unsubstituted arylsulfonyl(s) ((s)

Aryl sulfoxy), a substituted or unsubstituted alkenyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted amine group, a substituted or unsubstituted arylphosphino group, a substituted or unsubstituted phosphinoxide group, a substituted or unsubstituted Aryl group, or a substituted or unsubstituted heterocyclic group,

l1 and L2 are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted 2-valent heterocyclic group,

ar1 and Ar2 are each independently a nitrile group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted arylphosphino group, a substituted or unsubstituted phosphinoxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

a. b, d and e are each independently an integer of 0 to 4,

c and f are each independently an integer of 0 to 3,

z1 and z2 are each independently an integer from 0 to 4,

z1+ z2 is an integer from 1 to 4,

when a to f are each independently 2 or more, the substituents in parentheses may be the same or different from each other, or substituents adjacent to each other may be bonded to each other to form a ring.

In addition, one embodiment of the present specification provides an organic light-emitting device including: an anode, a cathode, and one or more organic layers disposed between the anode and the cathode, wherein one or more of the organic layers include a compound of formula 1.

Effects of the invention

The compound described in this specification can be used as a material for an organic layer of an organic light-emitting device. The compound according to at least one embodiment may achieve an improvement in efficiency, a low driving voltage, or a lifetime characteristic in an organic light emitting device.

The compound described in this specification can be used as a material for an electron injection layer, an electron transport layer, or an electron control layer.

Drawings

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

< description of symbols >

1: substrate

2: anode

3: luminescent layer

4: cathode electrode

5: hole transport layer

6: electron injection layer

7: electron transport layer

8: electronically regulated layer

Detailed Description

The present specification will be described in more detail below.

In the present specification, examples of the substituent are described below, but the present invention 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.

The term "substituted or unsubstituted" in the present specification means that the substituent is substituted with 1 or 2 or more substituents selected from deuterium, a halogen group, a cyano group, a silyl 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 bonded, 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, examples of the halogen group include fluorine (F), chlorine (Cl), bromine (Br), and iodine (I).

In the present specification, the silyl group may be represented by the formula of — SiRaRbRc, and the above Ra, Rb and Rc may each be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. 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 the present specification, the number of carbon atoms of the ester group is not particularly limited, but is preferably 1 to 50. Specifically, the compound may be represented by the following structural formula, but is not limited thereto.

In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 50. Specifically, the compound may have the following structure, 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 30. Specifically, the compound may have the following structure, but is not limited thereto.

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

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, isopropyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, benzyloxy, p-methylbenzyloxy and the like, but is not limited thereto.

In this specification, the boron group may be-BR₁₀₀R₁₀₁R is as defined above₁₀₀And R₁₀₁The same or different, may each be independently selected from the group consisting of hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group of carbon number 3 to 30, a substituted or unsubstituted linear or branched alkyl group of carbon number 1 to 30, a substituted or unsubstituted monocyclic or polycyclic aryl group of carbon number 6 to 30, and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group of carbon number 2 to 30.

In the present specification, specific examples of the phosphine oxide group include a diphenylphosphine oxide group, a dinaphthylphosphine oxide group and the like, but the phosphine oxide group is not limited thereto.

In the present specification, the amine group may be selected from-NH₂The number of carbon atoms of the alkylamino group, the N-arylalkylamino group, the arylamino group, the N-arylheteroarylamino group, the N-alkylheteroarylamino group and the heteroarylamino group is not particularly limited, but is preferably 1 to 30. Specific examples of the amino group include, but are not limited to, a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, a phenylamino group, a naphthylamino group, a biphenylamino group, an anthrylamino group, a 9-methylanthrylamino group, a diphenylamino group, an N-phenylnaphthylamino group, a ditolylamino group, an N-phenyltolylamino group, and a triphenylamino 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 40 carbon atoms. According to another embodiment, the alkyl group has 1 to 20 carbon atoms. Specific examples thereof include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methylbutyl group, 1-ethylbutyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl-2-pentyl group, 3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2-dimethylheptyl group, 1-ethyl-propyl group, 1-dimethyl-propyl group, 1-, Isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples thereof include, but are not limited to, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylethen-1-yl, 2-diphenylethen-1-yl, 2-phenyl-2- (naphthalen-1-yl) ethen-1-yl, 2-bis (biphenyl-1-yl) ethen-1-yl, stilbenyl, styryl and the like.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 40 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. Specifically, there may be mentioned, but not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like.

In the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 60. According to one embodiment, the aryl group has 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, or the like, but is not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 10 to 60. According to one embodiment, the aryl group has 10 to 30 carbon atoms. Specifically, the polycyclic aryl group may be a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a perylene group,

And a fluorenyl group, but is not limited thereto.

In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

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

And the like. But is not limited thereto.

In the present specification, the aryl group in the aryloxy group, arylthio group, arylsulfonyl group, arylphosphino group, and arylamino group can be applied to the aryl group described above.

In the present specification, the alkyl group in the alkylthio group, the alkylsulfonyl group, the alkylamino group, and the N-alkylheteroarylamino group can be applied to the above description of the alkyl group. Examples of the alkylthio group include a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group, and an octylthio group, and examples of the alkylsulfonyl group include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, and a butylsulfonyl group, but the alkylsulfanyl group is not limited thereto.

In the present specification, the heterocyclic group includes N, O, S, Si and 1 or more of 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. According to another embodiment, the number of carbon atoms of the heterocyclic group is 2 to 20. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,

Azolyl group,

Oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, triazolyl, and triazolyl,Acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo

Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, dibenzofuryl, benzofuryl, phenanthrolinyl, thiazolyl, and isoquinoyl

Azolyl group,

Examples of the organic solvent include, but are not limited to, an organic solvent such as ethanol, and the like.

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

In the present specification, the heteroaryl group in the heteroaryl group and the heteroarylamino group can be applied to the above description of the heterocyclic group.

In the present specification, an "adjacent" group means a substituent substituted on an atom directly connected to an atom substituted with the substituent, a substituent closest to the substituent in terms of a steric structure, or another substituent substituted on an atom substituted with the substituent. For example, 2 substituents substituted at the ortho (ortho) position in the phenyl ring and 2 substituents substituted on the same carbon in the aliphatic ring may be interpreted as groups "adjacent" to each other.

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.

In the present specification, 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 described above, except that the hydrocarbon ring has a valence of 1.

In the present specification, the aromatic hydrocarbon ring may be substituted with an aryl group except that the aromatic hydrocarbon ring has a valence of 1.

In the present specification, the heterocyclic ring contains 1 or more heteroatoms other than carbon atoms, specifically, the heteroatoms may contain 1 or more atoms selected from N, O, P, S, Si, Se and the like. The heterocyclic ring may be monocyclic or polycyclic, and may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and the aromatic heterocyclic ring may be selected from the heteroaryl groups described above, except that it has a valence of 1.

In one embodiment of the present specification, the chemical formula 1 is represented by any one of the following chemical formulae 1-1 to 1-4.

[ chemical formula 1-1]

[ chemical formulas 1-2]

[ chemical formulas 1-3]

[ chemical formulas 1 to 4]

In chemical formulas 1-1 to 1-4,

x1, L1, Ar1, R1 to R6 and a to f are the same as defined above.

In one embodiment of the present specification, chemical formula 1 is represented by any one of chemical formulae 2-1 to 2-4 below.

[ chemical formula 2-1]

[ chemical formula 2-2]

[ chemical formulas 2-3]

[ chemical formulas 2-4]

In chemical formulas 2-1 to 2-4,

x1, L2, Ar2, R1 to R6 and a to f are the same as defined above.

In one embodiment of the present specification, R1 to R6 are each independently hydrogen, deuterium, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amide group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted alkylsulfonyl group, a substituted or unsubstituted arylsulfonyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted amine group, a substituted or unsubstituted arylphosphine group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R1 to R6 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.

In one embodiment of the present specification, R1 to R6 are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted amine group having 1 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

In one embodiment of the present specification, R1 to R6 are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted amine 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.

In one embodiment of the present specification, R1 to R6 are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted amine group having 1 to 15 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.

In one embodiment of the present specification, R1 to R6 are each independently hydrogen or deuterium.

In one embodiment of the present specification, L1 and L2 are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted 2-valent heterocyclic group.

In one embodiment of the present specification, L1 and L2 are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 valences and 2 to 60 carbon atoms.

In one embodiment of the present specification, L1 and L2 are each independently 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.

In one embodiment of the present specification, L1 and L2 are each independently 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.

In one embodiment of the present specification, L1 and L2 are each independently a direct bond, or a substituted or unsubstituted arylene group having 6 to 15 carbon atoms.

In one embodiment of the present disclosure, L1 and L2 are each independently a direct bond or a phenylene group.

According to an embodiment of the present description, Ar1 and Ar2 are each independently a nitrile group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl phosphine group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

According to an embodiment of the present specification, Ar1 and Ar2 are each independently a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl phosphine group having 6 to 60 carbon atoms, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

According to an embodiment of the present specification, Ar1 and Ar2 are each independently a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl phosphine group having 6 to 30 carbon atoms, a substituted or unsubstituted phosphine oxide 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, Ar1 and Ar2 are each independently a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl phosphine group having 6 to 20 carbon atoms, a substituted or unsubstituted phosphine oxide 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 specification, Ar1 and Ar2 are each independently a phosphine oxide group substituted or unsubstituted with an aryl 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 specification, Ar1 and Ar2 are each independently a diarylphosphine oxide group having 12 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

According to an embodiment of the present description, Ar1 and Ar2 are each independently any one selected from the following structural formulae.

In the above-mentioned structural formula, the polymer,

y1 to Y3 are each independently N or CR',

at least one of Y1 to Y3 is N,

l3 and L4 are each independently a direct bond, or a substituted or unsubstituted arylene group,

ar3 and Ar4 are each independently hydrogen, deuterium, a nitrile group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted arylphosphino group, a substituted or unsubstituted phosphinoxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

a1 to A10 and R' are each independently hydrogen, deuterium, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amide group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted alkylsulfonyl group, a substituted or unsubstituted arylsulfonyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted amine group, a substituted or unsubstituted arylphosphino group, a substituted or unsubstituted phosphinoxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

a1, a2, a9 and a10 are each independently integers of 0 to 5,

a3, a7, and a8 are each independently integers from 0 to 7,

a4 to a6 are each independently an integer of 0 to 4,

a1 to a10 are each independently an integer of 2 or more, and the substituents in parentheses are the same as or different from each other,

is the site of binding.

According to an embodiment of the present description, a9, a10 and R' are hydrogen.

According to an embodiment of the present description, each of a1 to A8 is independently hydrogen, or a substituted or unsubstituted aryl.

According to an embodiment of the present description, each of a1 to A8 is independently hydrogen, phenyl, biphenyl, or naphthyl.

According to one embodiment of the present description, L3 and L4 are each independently a direct bond, phenylene, naphthylene, or biphenylene.

According to an embodiment of the present description, Ar3 and Ar4 are each independently a nitrile group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl phosphine group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

According to an embodiment of the present specification, Ar3 and Ar4 are each independently a nitrile group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

According to an embodiment of the present description, Ar3 and Ar4 are each independently a nitrile group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

According to an embodiment of the present description, Ar3 and Ar4 are each independently a nitrile group; a phenyl group; a biphenyl group; a naphthyl group; a triphenylene group; phenanthryl; a fluorenyl group substituted with a phenyl group and a methyl group, a pyridyl group, a dibenzofuranyl group, a dibenzothienyl group, or a carbazolyl group substituted with an aryl group or unsubstituted.

According to an embodiment of the present specification, the compound represented by the above chemical formula 1 has any one of the following structures.

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

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

An embodiment of the present specification provides an organic light emitting device including: the organic light-emitting device includes an anode, a cathode, and one or more organic layers disposed between the anode and the cathode, wherein one or more of the organic layers include the compound.

The organic light-emitting device of the present specification may have a single-layer structure or a multilayer structure in which two or more organic layers are stacked. For example, the organic layer of the present specification may be composed of 1 to 3 layers. In addition, the organic light-emitting device of the present specification may have a structure including a hole injection layer, a light-emitting layer, an electron transport layer, and the like as an organic layer. However, the structure of the organic light emitting device is not limited thereto, and a smaller number of organic layers may be included.

In addition, according to an embodiment of the present disclosure, the organic layer may include an electron injection layer, an electron transport layer, or an electron adjustment layer, and the electron injection layer, the electron transport layer, or the electron adjustment layer may include the compound of chemical formula 1.

In one embodiment of the present specification, the organic light-emitting device may further include 1 or 2 or more layers selected from the group consisting of a hole injection layer and a hole transport layer.

Specifically, in one embodiment of the present specification, the compound may be contained in 1 of the 2 or more electron injection layers, electron transport layers, or electron control layers, or may be contained in each of the 2 or more electron injection layers, electron transport layers, or electron control layers.

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

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

In another embodiment, the organic light emitting device may be an inverted (inverted) type organic light emitting device in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate.

For example, fig. 1 shows an example of the structure of an organic light-emitting device according to an embodiment of the present specification.

Fig. 1 illustrates a structure of an organic light emitting device in which a substrate 1, an anode 2, a hole transport layer 5, a light emitting layer 3, an electron adjusting layer 8, an electron transport layer 7, an electron injection layer 6, and a cathode 4 are sequentially stacked. In such a structure, the above-described compound may be contained in the above-described electron regulation layer 8, the electron transport layer 7, or the electron injection layer 6.

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

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

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

For example, the organic light emitting device of the present specification can be manufactured by sequentially stacking an anode, an organic layer, and a cathode on a substrate. In this case, the following production can be performed: the organic el device is manufactured by depositing a metal, a conductive metal oxide, or an alloy thereof on a substrate by a Physical Vapor Deposition (PVD) method such as a sputtering method or an electron beam evaporation method, forming an anode, forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer on the anode, and then depositing a substance that can be used as a cathode on the organic layer.

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

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

The anode material is preferably a material having a large work function in order to smoothly inject holes 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 SnO₂A combination of a metal such as Sb and an oxide; 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.

Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof, L iF/Al, or L iO₂And a multilayer structure material such as Al, but not limited thereto.

The hole injection layer is a layer for injecting holes from the electrode, and the following compounds are preferable as the hole injection substance: the organic light-emitting device has an ability to transport holes, has a hole injection effect from an anode, has an excellent hole injection effect for a light-emitting layer or a light-emitting material, prevents excitons generated in the light-emitting layer from migrating to an electron injection layer or an electron injection material, and has excellent thin film formation ability. Preferably, the HOMO (highest occupied molecular orbital) of the hole injecting substance is 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 (porphyrin), oligothiophene, arylamine-based organic substances, hexanitrile-hexaazatriphenylene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers.

The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer, and the hole transport substance is a substance that can receive holes from the anode or the hole injection layer and transport the holes to the light-emitting layer, and is preferably a substance 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.

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. Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq3), carbazole-based compound, dimerized styryl-based compound, BALq, and 10-hydroxybenzoquinoline-metallated compoundCompound, benzo

Examples of the polymer include, but are not limited to, oxazoles, benzothiazole and benzimidazole-based compounds, poly (p-phenylene vinylene) (PPV) -based polymers, spiro (spiro) compounds, polyfluorenes, and rubrenes.

The electron transporting layer is a layer that receives electrons from the electron injecting layer and transports the electrons to the light emitting layer, and the electron transporting material is preferably a material that can inject electrons from the cathode to the light emitting layer well and transfer the electrons to the light emitting layer, in addition to the compound according to one embodiment of the present specification. Specific examples thereof include, but are not limited to, Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic radical compounds, and hydroxyflavone-metal complexes. The electron transport layer may be used with any desired cathode material as used in the art. Examples of suitable cathode substances are, in particular, the customary substances having a low work function and accompanied by an aluminum or silver layer. In particular cesium, barium, calcium, ytterbium and samarium, in each case accompanied by an aluminum or silver layer.

The electron injection layer is a layer for injecting electrons from an electrode, and the electron injection material is preferably a compound other than the compound according to one embodiment of the present specification, the compound being: has an ability to transport electrons, an electron injection effect from a cathode, an excellent electron injection effect with respect to a light-emitting layer or a light-emitting material, prevents excitons generated in the light-emitting layer from migrating to a hole-injecting layer, and is excellent in thin-film formability. 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 is 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 electron control layer is a layer that prevents holes from reaching the cathode, and the electron control layer can be formed under the same conditions as the hole injection layer except for the compound according to one embodiment of the present specification. 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 specification 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

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

Production example 1

General production example 1

In the above reaction formula, X1 is S or O, and X is a leaving group (leaving group).

SM1(1eq) of the following table 1 was dissolved in THF (Tetrahydrofuran ), the Temperature was reduced to-78 ℃, then 2.5M N-Bu L i (N-butyllithium, N-Buthyl L itium) (1,4eq) was added dropwise, after 30 minutes 10H-spiro [ anthracene-9, 9' fluoren ] -10-one (SM 2 of the following table 1) (1eq) was added, after warming to Room Temperature (Room Temperature, RT) was stirred for 1 hour, 1N HCl (excess) was added, after stirring for 30 minutes, layer separation was performed, after removal of the solvent, purification with ethyl acetate was performed, then the obtained solid was put into acetic acid (excess), then sulfuric acid was added dropwise (cat.), the Temperature was reduced to Room Temperature, after neutralization with water, the filtered solid was recrystallized with Tetrahydrofuran and ethyl acetate, thereby producing a1 to 3892B and 38764B as shown in the following table 1.

[ Table 1]

General production example 2

After dissolving SM1(1eq) of table 2 in THF, the temperature was reduced to-78 ℃, then 2.5M N-Bu L i (1,4eq) was added dropwise, after 30 minutes anthracene-9, 10-dione (SM 2 of table 2) (1eq) was added, after raising to RT and stirring for 1 hour, 1N HCl (excess) was added, after stirring for 30 minutes, layer separation was performed, after removing the solvent, purification was performed with ethyl acetate, then the obtained solid was put into acetic acid (excess), then sulfuric acid (cat.) was added dropwise, stirring was refluxed, the temperature was reduced to normal temperature, after neutralization with water, the filtered solid was recrystallized with tetrahydrofuran and ethyl acetate, and thus an intermediate was produced.

C1 to C4 and D1 to D4 were produced as shown in table 3 below, except that SM1 and SM2 of table 3 were used instead of SM1 and anthracene-9, 10-dione of table 2, respectively, and the procedure as described above was further performed.

[ Table 2]

[ Table 3]

General production example 3

Any one (1eq) of a1 to a4, B1 to B4, C1 to C4, and D1 to D4, bis (pinacolato) diboron (1.4eq), and potassium acetate (3eq) synthesized in general production examples 1 and 2 was charged to 200m L of 1, 4-diboron

To the alkane, (dibenzylideneacetone) palladium (0.02 mol%) and tricyclohexylphosphine (0.04 mol%) were added under reflux with stirring, and the mixture was stirred under reflux. At the end of the reaction, the mixture was cooled to room temperature and filtered through celite. The filtrate was concentrated under reduced pressure, and chloroform was added to the residue to dissolve the filtrate, followed by washing with water, separating the organic layer, and drying with anhydrous Magnesium sulfate (Magnesium sulfate). This was distilled under reduced pressure, and stirred with ethyl acetate and ethanol, whereby A1-1 to A4-1, B1-1 to B4-1, C1-1 to C4-1, and D1-1 to D4-1 were produced as shown in Table 4 below.

[ Table 4]

Production example 2

General production example 4

In the above reaction formula, X1 is S or O, L1, L2, Ar1, Ar2, z1 and z2 are the same as defined in chemical formula 1.

After A1-1 to A4-1, B1-1 to B4-1, C1-1 to C4-1, D1-1 to D4-1 (SM 1, 1eq of Table 5), a secondary azine derivative and a heteroaryl derivative (1.1eq) as SM2 of Table 5 synthesized in general production example 3 were added to tetrahydrofuran (300ml), a 2M aqueous potassium carbonate solution (150ml) was added, tetrakis (triphenylphosphine) palladium (2 mol%) was added, and then stirred with heating for 10 hours. And (3) cooling to normal temperature, removing the potassium carbonate aqueous solution after the reaction is finished, and carrying out layer separation. After the solvent was removed, vacuum distillation was performed, and recrystallization was performed using tetrahydrofuran and ethyl acetate, thereby producing compounds 1 to 24 as shown in table 5 below.

[ Table 5]

Example 1

ITO (indium tin oxide) is added

The glass substrate (corning 7059 glass) coated with a thin film was put in distilled water in which a dispersant was dissolved, and washed with ultrasonic waves. The detergent used was a product of Fisher Co, and the distilled water used was distilled water obtained by twice filtering with 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, ultrasonic washing was performed in the order of solvents of isopropyl alcohol, acetone, and methanol, and then dried.

On the ITO transparent electrode thus prepared, hexanitrile hexaazatriphenylene (hexanitrile hexaazatriphenylene) was added

The thickness of (3) was subjected to thermal vacuum evaporation to form a hole injection layer. On the hole injection layer, HT1 as a hole transport substance was vacuum-evaporated

Then, HT2 was formed in a film thickness on the hole transport layer

Vacuum evaporation was performed to form a hole-regulating layer. As a compound light-emitting layer, a host BH1 and a dopant BD1 compound (weight ratio based on 25:1) were added

Vacuum evaporation is performed to a thickness of (1). Then, ETM1 Compound was allowed to stand

Formed as an electron adjusting layer, compounds 3 and L iQ synthesized in general production example 4 (weight ratio basis 1:1,

) Performing co-evaporation to form an electron transport layer, and sequentially forming lithium fluoride (L iF) on the electron transport layer

And Mg and Ag (10: 1 on a weight basis,

) Performing evaporation

The cathode is formed of aluminum in a thickness, thereby fabricating an organic light emitting device.

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

Maintenance of lithium fluoride

Deposition rate of (3), aluminum maintenance

The deposition rate of (3).

Example 2

An experiment was performed in the same manner as in example 1 except that compound 9 was used instead of compound 3 as the electron transport layer.

Example 3

An experiment was performed in the same manner as in example 1 except that compound 10 was used instead of compound 3 as the electron transport layer.

Example 4

An experiment was performed in the same manner as in example 1 except that compound 13 was used instead of compound 3 as the electron transport layer.

Example 5

An experiment was performed in the same manner as in example 1 except that compound 14 was used instead of compound 3 as the electron transport layer.

Example 6

An experiment was carried out in the same manner as in example 1 except that compound 9 was used as the electron transport layer in place of compound 3 in a weight ratio of 1:2 to L iQ.

Example 7

An experiment was performed in the same manner as in example 1 except that the electron transport layer was used in a weight ratio of 2:1 to L iQ.

Example 8

An experiment was performed in the same manner as in example 1 except that compound 13 was used as the electron transport layer in place of compound 3 in a weight ratio of L iQ of 2: 1.

Example 9

An experiment was performed in the same manner as in example 1 except that compound 24 was used instead of compound 3 as the electron transport layer.

Comparative example 1

An experiment was performed in the same manner as in example 1 except that ETM2 was used instead of compound 3 as the electron transport layer.

Comparative example 2

An experiment was performed in the same manner as in example 1 except that ETM4 was used instead of compound 3 as the electron transport layer.

Comparative example 3

An experiment was performed in the same manner as in example 1 except that ETM5 was used instead of compound 3 as the electron transport layer.

Comparative example 4

An experiment was performed in the same manner as in example 1, except that ETM2 was used in place of compound 3 as the electron transport layer and the weight ratio to L iQ was 2: 1.

The results of experiments conducted on the organic light-emitting devices manufactured using the respective compounds as the electron transport layer substances as shown in examples 1 to 9 and comparative examples 1 to 4 described above are shown in table 6.

[ Table 6]

Example 10 ITO (indium tin oxide) was treated with

On the ITO transparent electrode thus prepared, hexanitrile hexaazatriphenylene (HI-1) was added

Then, HT2 was formed in a film thickness on the hole transport layer

Vacuum evaporation was performed to form a hole-regulating layer. As a compound light-emitting layer, a compound (25: 1 by weight) containing a host BH1 and a dopant BD1 was used

Vacuum evaporation is performed to a thickness of (1). Then, compound 1 synthesized in general production example 4 was reacted

Formed as an electronically regulated layer, was coated with ETM2 and L iQ (weight basis 1:1,

And Mg and Ag (10: 1 on a weight basis,

) Performing evaporation

Maintenance of lithium fluoride

Deposition rate of (3), aluminum maintenance

The deposition rate of (3).

Example 11

An experiment was performed in the same manner as in example 10 except that compound 2 was used instead of compound 1 as the electron control layer.

Example 12

An experiment was performed in the same manner as in example 10 except that compound 4 was used instead of compound 1 as the electron control layer.

Example 13

An experiment was performed in the same manner as in example 10 except that compound 5 was used instead of compound 1 as the electron control layer.

Example 14

In example 10, an experiment was performed by the same method except that in the electron transport layer, L iQ was used in a ratio of 2:1 (wt%) as an electron transport layer, and compound 6 was used instead of compound 1 as an electron adjustment layer.

Example 15

An experiment was performed in the same manner as in example 10 except that compound 7 was used instead of compound 1 as the electron control layer.

Example 16

An experiment was performed in the same manner as in example 10 except that compound 8 was used instead of compound 1 as the electron control layer.

Example 17

An experiment was performed in the same manner as in example 10 except that compound 11 was used instead of compound 1 as the electron control layer.

Example 18

An experiment was performed in the same manner as in example 10 except that compound 12 was used instead of compound 1 as the electron control layer.

Example 19

An experiment was performed in the same manner as in example 10 except that compound 15 was used instead of compound 1 as the electron control layer.

Example 20

In example 10, an experiment was performed by the same method except that in the electron transport layer, the ratio of L iQ was 1:2 (wt%), and the compound 16 was used as the electron control layer instead of the compound 1.

Example 21

An experiment was performed in the same manner as in example 10 except that compound 17 was used instead of compound 1 as the electron control layer.

Example 22

An experiment was performed in the same manner as in example 10 except that compound 18 was used instead of compound 1 as the electron control layer.

Example 23

An experiment was performed in the same manner as in example 10 except that compound 19 was used instead of compound 1 as the electron control layer.

Example 24

An experiment was performed in the same manner as in example 10 except that compound 20 was used instead of compound 1 as the electron control layer.

Example 25

An experiment was performed in the same manner as in example 10 except that compound 21 was used instead of compound 1 as the electron control layer.

Example 26

An experiment was performed in the same manner as in example 10 except that compound 22 was used instead of compound 1 as the electron control layer.

Example 27

In example 10, an experiment was performed by the same method except that compound 3 was used as the electron transport layer in place of ETM2 in a ratio of 2:1 (wt%) to L iQ.

Example 28

An experiment was performed in the same manner as in example 10, except that compound 13 was used in place of ETM2 as the electron transport layer and compound 9 was used in place of compound 1 as the electron control layer.

Example 29

An experiment was performed in the same manner as in example 10 except that compound 23 was used instead of compound 1 as the electron control layer.

Comparative example 5

An experiment was performed in the same manner as in example 10 except that ETM3 was used instead of compound 1 as the electron control layer.

Comparative example 6

An experiment was performed in the same manner as in example 10 except that ETM4 was used instead of compound 1 as the electron control layer.

Comparative example 7

An experiment was performed in the same manner as in example 10 except that ETM5 was used instead of compound 1 as the electron control layer.

Comparative example 8

In example 10, an experiment was performed by the same method except that in the electron transport layer, the ratio of L iQ was 2:1 (wt%), and in the electron adjustment layer, ETM3 was used instead of Compound 1.

The results of experiments conducted on organic light-emitting devices manufactured using the respective compounds as the electron regulating layer and electron transporting layer substances as shown in examples 10 to 29 and comparative examples 5 to 8 described above are shown in table 7.

[ Table 7]

As can be seen from the above table, the compound derivatives of the chemical formula according to the present invention may play a role in electron transport and electron modulation in organic electronic devices represented by organic light emitting devices, and the devices according to the present invention show excellent characteristics in efficiency, driving voltage, stability. In particular, as a result of observation of comparative examples, the spiro-structured compound used in this document has a great advantage in terms of lifetime, and a heteroaryl group suitable for electron transport and electron modulation is introduced into a substituent in the same spiro structure, whereby high device performance can be obtained.

Claims

1. A compound represented by the following chemical formula 1:

chemical formula 1

In the chemical formula 1, the first and second,

x1 is O or S,

r1 to R6 are each independently hydrogen, deuterium, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amide group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted alkylsulfonyl group, a substituted or unsubstituted arylsulfonyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted amine group, a substituted or unsubstituted arylphosphino group, a substituted or unsubstituted phosphinoxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

a. b, d and e are each independently an integer of 0 to 4,

c and f are each independently an integer of 0 to 3,

z1 and z2 are each independently an integer from 0 to 4,

z1+ z2 is an integer from 1 to 4,

when a to f are each independently 2 or more, the substituents in parentheses may be the same or different from each other, or adjacent substituents may be bonded to each other to form a ring.

2. The compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulae 1-1 to 1-4:

chemical formula 1-1

Chemical formula 1-2

Chemical formulas 1 to 3

Chemical formulas 1 to 4

In chemical formulas 1-1 to 1-4,

x1, L1, Ar1, R1 to R6 and a to f are as defined in claim 1.

3. The compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulae 2-1 to 2-4:

chemical formula 2-1

Chemical formula 2-2

Chemical formula 2-3

Chemical formula 2-4

In chemical formulas 2-1 to 2-4,

x1, L2, Ar2, R1 to R6 and a to f are as defined in claim 1.

4. The compound of claim 1, wherein L1 and L2 are each independently a direct bond or a phenylene group.

5. The compound of claim 1, wherein each of Ar1 and Ar2 is independently selected from any one of the following structural formulae:

y1 to Y3 are each independently N or CR',

at least one of Y1 to Y3 is N,

a1, a2, a9 and a10 are each independently integers of 0 to 5,

a3, a7, and a8 are each independently integers from 0 to 7,

a4 to a6 are each independently an integer of 0 to 4,

is the site of binding.

6. The compound according to claim 1, wherein the compound represented by chemical formula 1 is any one of the following structures:

7. an organic light-emitting device, comprising: an anode, a cathode, and one or more organic layers disposed between the anode and cathode, one or more of the organic layers comprising the compound of any one of claims 1-6.

8. The organic light emitting device according to claim 7, wherein the organic layer comprises an electron injection layer, an electron transport layer, or an electron regulation layer comprising the compound of formula 1.