CN107459466B

CN107459466B - Compound and organic electronic element comprising same

Info

Publication number: CN107459466B
Application number: CN201710407382.3A
Authority: CN
Inventors: 河宰承; 洪性佶; 李成宰
Original assignee: LG Chem Ltd
Current assignee: LG Chem Ltd
Priority date: 2016-06-02
Filing date: 2017-06-02
Publication date: 2020-10-27
Anticipated expiration: 2037-06-02
Also published as: KR101917953B1; CN107459466A; KR20170136980A

Abstract

The present invention relates to a compound and an organic electronic device comprising the same. The compound of the present specification is used for an organic electronic device represented by an organic light-emitting device, and can reduce a driving voltage of the organic electronic device, improve light efficiency, and improve life characteristics of the device by thermal stability of the compound.

Description

Compound and organic electronic element comprising same

Technical Field

This application claims priority to korean patent application No. 10-2016-0069087, filed by the korean patent office at 2016, 06, 02, the contents of which are all incorporated herein by reference.

The present specification relates to a compound and an organic electronic element comprising the same.

Background

A typical example of the organic electronic device is an organic light-emitting device. In general, the organic light emission phenomenon is a phenomenon in which electric energy is converted into light energy by using an organic substance. An organic light emitting element utilizing an organic light emitting phenomenon generally has a structure including an anode and a cathode with an organic layer interposed therebetween. In order to improve the efficiency and stability of the organic light-emitting element, the organic layer may be formed of a multilayer structure formed of different materials, and may be formed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, or the like. In the structure of such an organic light emitting element, when a voltage is applied between both electrodes, holes are injected from the anode into the organic layer, electrons are injected from the cathode into the organic layer, and excitons (exiton) are formed when the injected holes and electrons meet each other, and light is emitted when the excitons transition to the ground state again.

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

Documents of the prior art

Patent document

International patent application publication No. 2003-012890

Disclosure of Invention

The present specification provides a compound and an organic electronic element comprising the same.

The present specification provides a compound represented by the following chemical formula 1 or 2.

[ chemical formula 1]

[ chemical formula 2]

In the above chemical formula 1 or 2,

q is a substituted or unsubstituted, mono-or polycyclic aliphatic hydrocarbon ring,

l1 is a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,

ar1 is hydrogen, deuterium, a halogen group, 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) (R))

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

Aryl thio), substituted or unsubstituted alkyl sulfoxide group(s) ((s)

Alkylsulfoxy), substituted or unsubstituted alkenyl, substituted or unsubstituted silyl, substituted or unsubstituted boryl, substituted or unsubstituted phosphinoxide, substituted or unsubstituted amineA substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

r1 to R6 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, 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 alkylsulfoxide group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted amine group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

n1 is an integer from 1 to 5,

n2 is an integer from 1 to 5,

n3 is an integer from 1 to 4,

n4 is an integer from 1 to 3,

n5 is an integer from 1 to 3,

n6 is an integer from 1 to 4,

when n1 to n6 are 2 or more, the structures in parentheses of 2 or more are the same as or different from each other.

Further, the present specification provides an organic electronic element, comprising: the organic light-emitting device includes a first electrode, a second electrode provided so as to face the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contain the compound.

The compound according to one embodiment of the present specification is used for an organic electronic device typified by an organic light-emitting device, and can reduce a driving voltage of the organic electronic device, improve light efficiency, and improve life characteristics of the device by thermal stability of the compound.

Drawings

Fig. 1 illustrates an organic electronic component 10 according to one embodiment of the present description.

Fig. 2 shows an organic electronic component 11 according to another embodiment of the present description.

Description of the symbols

10. 11: organic light emitting element

20: substrate

30: a first electrode

40: luminescent layer

50: second electrode

60: hole injection layer

70: hole transport layer

80: electron blocking layer

90: electron transport layer

100: electron injection layer

Detailed Description

The present specification will be described in more detail below.

The present specification provides a compound represented by the above chemical formula 1.

The compounds represented by the above chemical formulas 1 and 2 have an effect of increasing triplet energy, improving hole transport ability, and improving device performance because Q has a monocyclic or polycyclic aliphatic hydrocarbon ring.

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

In this specification

Refers to the attachment site.

The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the substituted position is not limited as long as the hydrogen atom can be substituted, that is, the substituted position of the substituent, 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" as used herein means that the substituent is 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 amide group, an alkyl group, a cycloalkyl group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkylsulfoxide group, an alkenyl group, a silyl group, a boron group, a phosphine oxide group, an amine group, an arylamino group, an aryl group, and a heteroaryl group containing 1 or more substituents of N, O, S, Se and Si atoms, or is linked with 2 or more substituents among the above-exemplified substituents, or does not have any substituent.

In the present specification, examples of the halogen group include fluorine, chlorine, bromine, and iodine.

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 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 in the imide 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, with respect to the amino group, the nitrogen of the amino 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 alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. 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-methyl-butyl group, 1-ethyl-butyl 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 cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 40 carbon atoms, specifically, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentyl group, a2, 3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a2, 3-dimethylcyclohexyl group, a3, 4, 5-trimethylcyclohexyl group, a 4-tert-butylcyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like, but 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, there may be mentioned 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, benzyloxy, p-methylbenzyloxy and the like, but not limited thereto.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. 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, stilbene, and styryl.

In the present specification, the silyl group is a substituent comprising Si and directly bonded to the Si atom as a radical, and is represented by-SiR₁₀₄R₁₀₅R₁₀₆Is represented by R₁₀₄To R₁₀₆The same or different from each other, and each independently may be a substituent composed of at least one of hydrogen, deuterium, a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a cycloalkyl group, an aryl group, and a heterocyclic 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 this specification, the boron group may be-BR₁₀₀R₁₀₁R is as defined above₁₀₀And R₁₀₁The same or different from each other, and each independently may be selected from the group consisting of hydrogen, deuterium, halogen, 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, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 50. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl 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 40. 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,

Aryl, fluorenyl, etc., but notAnd is 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

Etc., but are 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 6 to 50. Examples of heteroaryl groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, thienyl,

Azolyl group,

Oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzopyrazinyl, pyrazinyl, triazinyl, pyrazinyl, carbazolyl, benzoxazolyl

Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthroline, thiazolyl, and isoquinoyl

Azolyl group,

Oxadiazolyl, thiadiazolyl, benzothiazolyl, dibenzofuranyl, and the like, but is not limited thereto.

In the present specification, amino means amino (-NH-)₂) With at least one hydrogen atom of the 1-valent amine substituted by another substituent, and with-NR₁₀₇R₁₀₈Is represented by R₁₀₇And R₁₀₈The same or different from each other, and each independently may be a substituent composed of at least one of hydrogen, deuterium, a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a cycloalkyl group, an aryl group, and a heterocyclic group (wherein, R is₁₀₇And R₁₀₈At least one of which is not hydrogen). For example, it may be selected from-NH₂The number of carbon atoms 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-methyl-anthrylamino group, a diphenylamino group, a ditolylamino group, an N-phenyltolylamino group, a triphenylamino group, an N-phenylbiphenylamino group, an N-phenylnaphthylamino group, an N-biphenylnaphthylamino group, an N-naphthylfluorenylamino group, an N-phenylphenanthrylamino group, an N-biphenylphenanthrylamino group, an N-phenylfluorenylamino group, an N-phenylterphenylamino group, an N-phenanthrylfluorenylamino group, and an N-biphenylfluorenylamino group.

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

In the present specification, aryloxy, arylthio(s) ((R))

Aryl thio) is the same as the Aryl exemplified above. Specifically, the aryloxy group includes phenoxy, p-tolyloxy, m-tolyloxy, 3, 5-dimethyl-phenoxy, 2,4, 6-trimethylphenoxy, p-tert-butylphenoxy, 3-biphenyloxy, 4-biphenyloxy, 1-naphthyloxy, 2-naphthyloxy, 4-methyl-1-naphthyloxy, 5-methyl-2-naphthyloxy, 1-anthracenyloxy, 2-anthracenyloxy, 9-anthracenyloxy, 1-phenanthrenyloxy, 3-phenanthrenyloxy, p-tolyloxy, p-tert-butylphenyloxy, p-tolyloxy, p-tolyl,Examples of the arylthio group include, but are not limited to, phenylthio, 2-methylphenylthio, and 4-tert-butylphenylthio.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. Arylamine groups containing 2 or more of the above-described aryl groups may contain monocyclic aryl groups, polycyclic aryl groups, or both monocyclic aryl groups and polycyclic aryl groups. For example, the aryl group in the arylamine group can be selected from the examples of the aryl group. Specific examples of the arylamine group include, but are not limited to, phenylamine, naphthylamine, biphenylamine, anthracenylamine, 3-methyl-phenylamine, 4-methyl-naphthylamine, 2-methyl-biphenylamine, 9-methyl-anthracenylamine, diphenylamino, phenylnaphthylamino, ditolylamino, phenyltolylamino, carbazole, and triphenylamino.

In the present specification, the arylene group means a group having two binding sites on the aryl group, that is, a 2-valent group. The above description of the aryl groups applies, except that they are each a 2-valent group.

In the present specification, heteroarylene means a group having two binding sites on a heteroaryl group, i.e., a 2-valent group. They are applicable to the description of the above-mentioned heteroaryl groups, except that they are each a 2-valent group.

In one embodiment of the present specification, Q is a substituted or unsubstituted, monocyclic or polycyclic, aliphatic hydrocarbon ring.

In one embodiment of the present specification, Q is substituted or unsubstituted cyclopentane, substituted or unsubstituted cyclohexane, substituted or unsubstituted cycloheptane, substituted or unsubstituted cyclooctane, substituted or unsubstituted bicycloheptane, substituted or unsubstituted tricycloheptane, or substituted or unsubstituted decalin.

In one embodiment of the present specification, Q is cyclopentane, substituted or unsubstituted with an alkyl or aryl group.

In one embodiment of the present specification, Q is cyclopentane, substituted or unsubstituted with methyl, ethyl, isopropyl, tert-butyl, or phenyl.

In one embodiment of the present description, Q is cyclopentane.

In one embodiment of the present specification, Q is cyclohexane substituted or unsubstituted with alkyl or aryl.

In one embodiment of the present specification, Q is cyclohexane substituted or unsubstituted with methyl, ethyl, isopropyl, tert-butyl or phenyl.

In one embodiment of the present specification, Q is cyclohexane.

In one embodiment of the present specification, Q is cycloheptane substituted or unsubstituted with alkyl or aryl.

In one embodiment of the present specification, Q is cycloheptane substituted or unsubstituted with methyl, ethyl, isopropyl, tert-butyl or phenyl.

In one embodiment of the present specification, Q is cycloheptane.

In one embodiment of the present specification, Q is cyclooctane, substituted or unsubstituted with an alkyl group or an aryl group.

In one embodiment of the present specification, Q is cyclooctane substituted or unsubstituted with methyl, ethyl, isopropyl, tert-butyl, or phenyl.

In one embodiment of the present specification, Q is cyclooctane.

In one embodiment of the present specification, Q is bicycloheptane substituted or unsubstituted with an alkyl or aryl group.

In one embodiment of the present specification, Q is bicycloheptane substituted or unsubstituted with methyl, ethyl, isopropyl, tert-butyl or phenyl.

In one embodiment of the present description, Q is bicycloheptane.

In one embodiment of the present specification, Q is tricycloheptane substituted or unsubstituted with an alkyl or aryl group.

In one embodiment of the present specification, Q is tricycloheptane substituted or unsubstituted with methyl, ethyl, isopropyl, tert-butyl or phenyl.

In one embodiment of the present description, Q is tricycloheptane.

In one embodiment of the present specification, Q is decahydronaphthalene substituted with an alkyl or aryl group or unsubstituted.

In one embodiment of the present specification, Q is decahydronaphthalene substituted or unsubstituted with methyl, ethyl, isopropyl, tert-butyl or phenyl.

In one embodiment of the present description, Q is decalin.

In one embodiment of the present specification, Q may be any one selected from the following structural formulae.

In one embodiment of the present specification, L1 is a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene.

In one embodiment of the present specification, L1 is a direct bond.

In one embodiment of the present specification, L1 is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted terphenylene group, or a substituted or unsubstituted fluorenylene group.

In one embodiment of the present specification, L1 is a 2-valent fluorenylene group substituted or unsubstituted with a methyl group, an ethyl group, or a tert-butyl group.

In one embodiment of the present specification, L1 is phenylene, biphenylene, naphthylene, terphenylene, or fluorenylene.

In one embodiment of the present specification, L1 is a substituted or unsubstituted 2-valent dibenzofuranyl group, a substituted or unsubstituted 2-valent dibenzothiophenyl group, or a substituted or unsubstituted 2-valent carbazolyl group.

In one embodiment of the present specification, L1 is a 2-valent carbazolyl group substituted or unsubstituted with a phenyl group.

In one embodiment of the present specification, L1 is a 2-valent dibenzofuranyl group, a 2-valent dibenzothiophenyl group, or a 2-valent carbazolyl group.

In one embodiment of the present specification, L1 is any one selected from the following structural formulae.

In one embodiment of the present specification, Ar1 is hydrogen, deuterium, a halogen group, 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 alkylsulfidenyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted phosphinoxide group, a substituted or unsubstituted amine group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, Ar1 is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms.

In one embodiment of the present specification, Ar1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted tetrabiphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted perylene group

A group, or a substituted or unsubstituted fluorenyl group.

In one embodiment of the present specification, Ar1 is phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, anthryl, phenanthryl, terphenylPhenyl, pyrenyl, perylenyl,

A phenyl group or a fluorenyl group.

In one embodiment of the present specification, Ar1 is a substituted or unsubstituted heteroaryl group having 6 to 50 carbon atoms.

In one embodiment of the present specification, Ar1 is a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

In one embodiment of the present specification, Ar1 is dibenzofuranyl substituted or unsubstituted with phenyl.

In one embodiment of the present specification, Ar1 is dibenzothienyl substituted or unsubstituted with phenyl.

In one embodiment of the present description, Ar1 is a dibenzofuranyl or dibenzothiophenyl group.

In one embodiment of the present specification, Ar1 is any one selected from the following structural formulae.

In one embodiment of the present specification, the above R' and R ″ are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, 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 alkylsulfidenyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphinoxide group, a substituted or unsubstituted amine group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, R1 to R6 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, 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 alkylsulfidenyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphinoxide group, a substituted or unsubstituted amine group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, R1 to R6 are the same as or different from each other, and each is independently hydrogen.

In one embodiment of the present specification, the chemical formula 1 may be represented by the following chemical formulae 3 to 6.

[ chemical formula 3]

[ chemical formula 4]

[ chemical formula 5]

[ chemical formula 6]

In the above-mentioned chemical formulas 3 to 6,

the definitions for Q, L1, Ar1, R1 to R6, and n1 to n6 are the same as those in the above chemical formula 1.

In one embodiment of the present specification, the chemical formula 2 may be represented by the following chemical formulae 7 to 10.

[ chemical formula 7]

[ chemical formula 8]

[ chemical formula 9]

[ chemical formula 10]

In the above-mentioned chemical formulas 7 to 10,

the definitions for Q, L1, Ar1, R1 to R6, and n1 to n6 are the same as those in the above chemical formula 2.

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

In one embodiment of the present specification, the chemical formula 2 may be any one selected from the following compounds.

The compound according to one embodiment of the present specification can be produced by a production method described later. Although representative examples are described in the production examples described later, a substituent may be added or deleted as necessary, or the position of the substituent may be changed. Further, starting materials, reaction conditions, and the like may be changed based on techniques known in the art.

Further, the present specification provides an organic electronic element comprising the above compound.

In one embodiment of the present specification, there is provided an organic light-emitting element including: a first electrode and a second electrode provided to face the first electrode; and 1 or more organic layers between the first electrode and the second electrode, wherein 1 or more of the organic layers contain the compound.

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 another member but also a case where another member exists between the two members.

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

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

According to one embodiment of the present specification, the organic light emitting element may be selected from an organic phosphorescent element, an organic solar cell, an Organic Photoreceptor (OPC), and an organic transistor.

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

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

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

In one embodiment of the present specification, the organic layer includes an electron blocking layer, and the electron blocking layer includes the compound.

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

In one embodiment of the present specification, the organic light-emitting element includes a first electrode, a second electrode provided so as to face the first electrode, a light-emitting layer provided between the first electrode and the second electrode, and 2 or more organic layers provided between the light-emitting layer and the first electrode or between the light-emitting layer and the second electrode, and at least one of the 2 or more organic layers includes the compound. In one embodiment of the present specification, the 2 or more organic layers may be 2 or more layers selected from an electron transport layer, an electron injection layer, a layer which simultaneously transports electrons and injects electrons, and a hole blocking layer.

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

In one embodiment of the present specification, when the 2 or more electron transport layers each contain the compound, materials other than the compound may be the same or different from each other.

In one embodiment of the present specification, the organic layer further includes a hole injection layer or a hole transport layer including a compound containing an arylamine group, a carbazole group, or a benzocarbazole group, in addition to the organic layer including the compound.

In another embodiment, the organic light-emitting element may be an organic light-emitting element having a structure (normal type) in which an anode, 1 or more organic layers, and a cathode are sequentially stacked on a substrate.

In the case where the organic layer including the compound of chemical formula 1 is an electron transport layer, the electron transport layer may further include an n-type dopant. The n-type dopant may be one known in the art, and for example, a metal or a metal complex may be used. According to one example, the electron transport layer including the compound of chemical formula 1 may further include LiQ.

In one embodiment of the present specification, the organic light-emitting element includes a first electrode, a second electrode provided so as to face the first electrode, a light-emitting layer provided between the first electrode and the second electrode, and 2 or more organic layers provided between the light-emitting layer and the first electrode or between the light-emitting layer and the second electrode, and at least one of the 2 or more organic layers includes the compound. In one embodiment of the present specification, the 2 or more organic layers may be 2 or more layers selected from a hole transport layer, a hole injection layer, a layer which simultaneously performs hole transport and electron injection, and a hole blocking layer.

In one embodiment of the present specification, the organic layer may have a stacked structure including a p-type doped layer.

In this specification, the p-type doped layer refers to a layer doped with a p-type dopant. The p-type dopant is a substance that imparts p-type semiconductor characteristics to the host substance. The p-type semiconductor property refers to a property of receiving hole injection or transporting holes at a HOMO (highest occupied molecular orbital) level, that is, a property of a substance having a large hole conductivity.

In one embodiment of the present specification, in the case where the organic layer including the compound of chemical formula 1 is a hole injection layer, the hole injection layer may be doped with a p-type dopant.

In one embodiment of the present specification, the p-type dopant may be a material known in the art, and the concentration of the doped layer may be 0.01 wt% to 50 wt%.

In one embodiment of the present description, a hole transport layer doped with a p-type dopant may be included between the light emitting layer and the anode. According to one example, a hole transport layer containing the compound 1 and doped with a dopant may be included between the light emitting layer and the anode. More specifically, a hole transport layer containing compound 1 and doped with a dopant may be included between the hole adjusting layer and the hole injection layer.

In another embodiment, the organic light emitting element may be an inverted (inverted) type organic light emitting element in which a cathode, 1 or more organic layers, and an anode are sequentially stacked on a substrate.

For example, the structure of the organic light-emitting element in the present specification may have the structures shown in fig. 1 and 2, but is not limited thereto.

Fig. 1 illustrates an example of the structure of an organic light-emitting element 10 in which a first electrode 30, a light-emitting layer 40, and a second electrode 50 are sequentially stacked on a substrate 20. Fig. 1 is an exemplary structure of an organic light-emitting element according to one embodiment of the present specification, and may further include another organic layer.

Fig. 2 illustrates an example of the structure of an organic light-emitting element in which a first electrode 30, a hole injection layer 60, a hole transport layer 70, an electron blocking layer 80, a light-emitting layer 40, an electron transport layer 90, an electron injection layer 100, and a second electrode 50 are sequentially stacked on a substrate 20. Fig. 2 is an exemplary structure according to an embodiment of the present disclosure, and may further include another organic layer.

The organic light-emitting element of the present specification can be manufactured using materials and methods known in the art, except that 1 or more of the organic layers contain the compound of the present specification, that is, the compound described above.

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

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

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

In addition, with respect to the compound of chemical formula 1, in the manufacture of the organic light emitting element, the organic layer may be formed not only by a vacuum evaporation method but also by a solution coating method. The solution coating method is not limited to spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roll coating, and the like.

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

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

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

The anode material is preferably a material having a large work function in order to smoothly inject holes into the organic layer. Specific examples of the anode material usable 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.

The cathode material is preferably a material having a small work function 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, or alloys thereof; LiF/Al or LiO₂And a multilayer structure material such as Al, but not limited thereto.

The hole injection layer is a layer for injecting holes from the electrode, and the following compounds are preferable as the hole injection substance: the organic light-emitting device has the ability to transport holes, has a hole injection effect from the anode, has an excellent hole injection effect for the light-emitting layer or the light-emitting material, prevents excitons generated in the light-emitting layer from migrating to the electron injection layer or the electron injection material, and has excellent thin film 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 material is a material that can receive holes from the anode or the hole injection layer and transport the holes to the light-emitting layer. Specific examples thereof include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers in which a conjugated portion and a non-conjugated portion are present simultaneously.

The electron blocking layer is a layer that prevents holes injected from the hole injection layer from passing through the light-emitting layer and entering the electron injection layer, and can improve the life and efficiency of the element.

The light-emitting substance in the light-emitting layer 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 a 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.

The light emitting layer may include a host material and a dopant material. The host material includes aromatic fused ring derivatives, heterocyclic 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, and the like, but are not limited thereto.

As the dopant material, there are aromatic amine derivatives, styryl amine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, the aromatic amine derivative is an aromatic fused ring derivative having a substituted or unsubstituted arylamine group, and includes pyrene, anthracene, perylene, and the like having an arylamine group,

Diindenoperene (Periflanthene) and the like, as the styrylamine compound, a compound in which at least 1 arylvinyl group is substituted on a substituted or unsubstituted arylamine, and which is substituted or unsubstituted with 1 or 2 or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamine group. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltrimethylamine, and styryltretramine. Further, as the metal complex, there are an iridium complex, a platinum complex and the like, but not limited thereto.

The electron transporting layer is a layer that receives electrons from the electron injecting layer and transports the electrons to the light emitting layer, and the electron transporting material is a material that can receive electrons from the cathode well and transfer the electrons to the light emitting layer, and a material having a high electron mobility is preferable. Specific examples thereof include Al complexes of 8-hydroxyquinoline and Al complexes containing Alq₃The complex of (a), an organic radical compound, a hydroxyflavone-metal complex, etc., but are not limited thereto. The electron transport layer may be used with any desired cathode material as used in the prior 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 the electrode, and is preferably a compound of: has electron transporting ability, electron injecting effect from cathode, and light emitting effectThe material has excellent electron injection effect, prevents excitons generated in the light-emitting layer from migrating to the hole-injecting layer, and has excellent thin-film-forming ability. Specifically, there are fluorenone, anthraquinone dimethane (Anthraquinodimethane), diphenoquinone, thiopyran dioxide, and,

Azole,

Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, metal complexes, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.

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

The hole-adjusting layer effectively receives holes from the hole-transporting layer, and plays a role of adjusting the mobility of holes, thereby adjusting the amount of holes transported to the light-emitting layer. Further, an electron barrier function of not causing electrons supplied from the light-emitting layer to transit to the hole-transporting layer can be performed at the same time. Which can increase luminous efficiency by maximizing the balance of holes and electrons in the light emitting layer, and can improve the lifespan of the element by electron stability of the hole adjusting layer, materials known in the art may be used.

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-injecting layer. Specifically, there are

Oxadiazole derivative or triazole derivative, phenanthroline derivative, BCP, and aluminum complexExamples of the substance include, but are not limited to, aluminum complex.

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

In one embodiment of the present specification, the compound represented by the above chemical formula 1 may be included in an organic solar cell or an organic transistor in addition to an organic light emitting element.

The compound according to the present specification can be applied to an organic electronic element typified by an organic phosphorescent element, an organic solar cell, an organic photoreceptor, an organic transistor, or the like by a principle similar to that when applied to an organic light-emitting element.

Hereinafter, examples, comparative examples and the like will be described in detail to specifically describe the present specification. However, the examples and comparative examples in the present specification may be modified into various other forms, and the scope of the present specification should not be construed as being limited to the examples and comparative examples described in detail below. The examples and comparative examples of the present specification are provided to more fully describe the present specification to those skilled in the art.

< production example >

< production example 1> -Synthesis of A1 to A4, B1 and B2

(1) Synthesis of A1

2-bromo-9H-fluorene (100g, 407.96mmol) and 50 wt% aqueous sodium hydroxide solution (70g, 897.51mol) were added to dimethyl sulfoxide (1000ml), and 1, 4-dibromobutane (88.09g, 407.96mmol) was added dropwise at 160 ℃, followed by heating and stirring for 3 hours. After completion of the reaction by lowering the temperature to room temperature, the reaction mixture was extracted with toluene (tolumen) and water, and then purified by column chromatography to obtain a1(120g, yield 98%) which was an ivory liquid as the above-mentioned compound.

MS[M+H]⁺＝299.14

(2) Synthesis of A2

A1(10g, 33.55mmol), 9 '-diphenyl-9H-fluoren-2-amine (11.29g, 33.89mmol) and sodium tert-butoxide (4.5g, 46.97mol) were placed in toluene (toluene), heated with stirring, then refluxed and [1,1' -bis (diphenylphosphino) ferrocene ] dichloropalladium (490mg, 2 mmol%) was placed. After the reaction was completed by lowering the temperature to normal temperature, recrystallization was performed using chloroform and ethyl acetate to obtain a 2.

MS[M+H]⁺＝552.26

(3) Synthesis of A3

A1(10g, 40.79mmol), 9 '-diphenyl-9H-fluoren-2-amine (13.87g, 41.61mmol) and sodium tert-butoxide (4.5g, 46.97mol) were placed in toluene (toluene), heated with stirring, then refluxed and [1,1' -bis (diphenylphosphino) ferrocene ] dichloropalladium (490mg, 2 mmol%) was placed in. After the reaction was completed by lowering the temperature to normal temperature, recrystallization was performed using chloroform and ethyl acetate to obtain a 3.

MS[M+H]⁺＝498.64

(4) Synthesis of A4

A1(10g, 25.17mmol), 9 '-diphenyl-9H-fluoren-2-amine (5.92g, 25.17mmol) and sodium tert-butoxide (4.5g, 46.97mol) were placed in toluene (toluene), heated with stirring, then refluxed and [1,1' -bis (diphenylphosphino) ferrocene ] dichloropalladium (490 mg.2mmol%) was placed. After the reaction was completed by lowering the temperature to normal temperature, recrystallization was performed using ethyl acetate and hexane (hexane) to produce a 4.

MS[M+H]⁺＝552.73

(5) Synthesis of B1

B1 was synthesized in the same manner except that 1, 5-dibromopentane was used instead of 1, 4-dibromobutane in the synthesis of a 1.

MS[M+H]⁺＝313.05

(6) Synthesis of B2

B1 was synthesized by the same method except that B1 was used instead of a1 in the synthesis of a 2.

MS[M+H]⁺＝566.28

< production example 2> -Synthesis of Compound 1

A2(15g, 27.16mmol), 4-iodobiphenyl (7.75g, 27.7mmol) and sodium tert-butoxide (3.57g, 38.02mmol) were placed in toluene (toluene), heated with stirring, then refluxed and charged with bis (tri-tert-butylphosphine) palladium (277 mg.2mmol%). After the reaction was completed by lowering the temperature to normal temperature, the reaction mixture was recrystallized from tetrahydrofuran and ethyl acetate to produce compound 1.

MS[M+H]⁺＝713.32

< production example 3> -Synthesis of Compound 2

Compound 2 was synthesized in the same manner as described above except that 2-bromo-9, 9-dimethyl-9H-fluorene was used instead of 4-iodobiphenyl in the synthesis of compound 1.

MS[M+H]⁺＝744.36

< production example 4> -Synthesis of Compound 3

Compound 3 was synthesized in the same manner as described above except that 2-bromo-9, 9-diphenyl-9H-fluorene was used instead of 4-iodobiphenyl in the synthesis of compound 1.

MS[M+H]⁺＝868.39

< production example 5> -Synthesis of Compound 4

Compound 4 was synthesized by the same method except that 4- (4-chlorophenyl) dibenzo [ b, d ] furan was used instead of 4-iodobiphenyl in the synthesis of compound 1.

MS[M+H]⁺＝794.33

< production example 6> -Synthesis of Compound 5

Compound 5 was synthesized in the same manner as described above except that B2 was used instead of a2 and 4-bromoterphenyl was used instead of 4-iodobiphenyl in the synthesis of compound 1.

MS[M+H]⁺＝794.37

< production example 7> -Synthesis of Compound 6

Compound 6 was synthesized in the same manner as in the synthesis of compound 1 above except that B2 was used instead of a2 and 4-chloro-1, 1:2,1 ″ -terphenyl was used instead of 4-iodobiphenyl.

MS[M+H]⁺＝794.37

< production example 8> -Synthesis of Compound 7

Compound 7 was synthesized by the same method except that B2 was used instead of a2 in the synthesis of compound 3.

MS[M+H]⁺＝882.40

< production example 9> -Synthesis of Compound 8

Compound 8 was synthesized in the same manner as in the synthesis of compound 1 above, except that B2 was used instead of a2 and 4- (4-chlorophenyl) dibenzo [ B, d ] thiophene was used instead of 4-iodobiphenyl.

MS[M+H]⁺＝824.33

< production example 10> -Synthesis of Compound 9

A2(15g, 27.21mmol), 3- (4-iodophenyl) -9-phenylcarbazole (9.82g, 27.75mmol) and sodium tert-butoxide (3.57g, 38.02mmol) were taken in toluene (toluene), heated with stirring, then refluxed and charged with [ bis (tri-tert-butylphosphino) ] palladium (277mg, 2 mmol%). After the reaction was completed by lowering the temperature to normal temperature, the reaction mixture was recrystallized from tetrahydrofuran and ethyl acetate to produce compound 9.

MS[M+H]⁺＝870.12

< production example 11> -Synthesis of Compound 10

A3(15g, 30.17mmol), 4-iodobiphenyl (10.26g, 30.77mmol) and sodium tert-butoxide (3.57g, 38.02mmol) were placed in toluene (toluene), heated with stirring, then refluxed and charged with [ bis (tri-tert-butylphosphine) ] palladium (277 mg.2mmol%). After the reaction was completed by lowering the temperature to normal temperature, the reaction mixture was recrystallized from tetrahydrofuran and ethyl acetate to produce compound 10.

MS[M+H]⁺＝650.84

< production example 12> -Synthesis of Compound 11

A4(15g, 27.18mmol), 4-iodobiphenyl (7.76g, 27.73mmol) and sodium tert-butoxide (3.57g, 38.02mmol) were placed in toluene (toluene), heated with stirring, then refluxed and charged with [ bis (tri-tert-butylphosphine) ] palladium (277 mg.2mmol%). After the reaction was completed by lowering the temperature to normal temperature, the reaction mixture was recrystallized from tetrahydrofuran and ethyl acetate to produce compound 11.

MS[M+H]⁺＝704.93

< example >

< example 1>

Will be provided with

A glass substrate (corning 7059 glass) coated with ITO (indium tin oxide) in a thick film was put in distilled water in which a dispersant was dissolved, and washed by ultrasonic waves. The detergent used was a product of fisher corporation (Fischer Co.) and the distilled water was filtered 2 times using a Filter (Filter) manufactured by Millipore Co. After washing the ITO for 30 minutes, ultrasonic washing was repeated 2 times with distilled water for 10 minutes. After the washing with distilled water is finished, ultrasonic washing is carried out by using isopropanol, acetone and methanol solvents in sequence, and drying is carried out.

On the ITO transparent electrode thus prepared

The hole injection layer was formed by thermally vacuum evaporating X1(hexanitrile hexaazatriphenylene). Vacuum evaporation on the hole injection layer

Compound 1 synthesized in production example 2 as a hole-transporting substance was then applied onto the hole-transporting layer

The hole control layer was formed by vacuum deposition of HT2 film thickness. As a compound light-emitting layer, to

The bulk H1 and dopant D1 compound (H1 is present at 98% volume ratio of the layer and D1 is present at 2% volume ratio of the layer) were vacuum evaporated to thickness of (1). Then, the E1 compound and LiQ were used in a volume ratio of 1:1

After forming the electron transport layer, sequentially evaporating

Lithium fluoride (LiF) and

the cathode is formed of aluminum in a thickness to manufacture an organic light emitting element.

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 3 was used as the hole transport layer instead of compound 1 synthesized in production example 2.

< example 3>

An experiment was performed in the same manner as in example 1 except that compound 6 was used as the hole transport layer instead of compound 1 synthesized in production example 2.

< example 4>

An experiment was performed in the same manner as in example 1 except that compound 9 was used as the hole transport layer instead of compound 1 synthesized in production example 2.

< example 5>

In example 1, an experiment was performed in the same manner as above except that HT1 was used as the hole transporting layer instead of compound 1 synthesized in production example 2, and that compound 5 was used as the hole adjusting layer instead of HT 2.

< example 6>

An experiment was performed in the same manner as in example 5 above, except that compound 7 was used as the hole controlling layer instead of compound 5 synthesized in production example 6.

< example 7>

An experiment was performed in the same manner as in example 5 above, except that compound 11 was used as the hole controlling layer instead of compound 5 synthesized in production example 6.

< example 8>

An experiment was performed in the same manner as in example 5 above, except that compound 10 was used as the hole controlling layer instead of compound 5 synthesized in production example 6.

< example 9>

On an ITO transparent electrode prepared in the same manner as in example 1

Compound 3 is thermally vacuum-deposited to a thickness to form a hole injection layer

X2 was doped at a concentration of 5% (Compound 3 was present in the layer at a volume ratio of 95%)X2 being present in the layer at a volume ratio of 5%) and the above-mentioned compound 3 as a hole transporting substance is vacuum-evaporated on the hole injecting layer

Then, the above-mentioned hole transport layer is covered with

The film thickness was vacuum-evaporated with HT2, thereby forming a hole regulating layer. As a compound light-emitting layer, to

Bulk H1 and dopant D1 compounds (in the layer, H1 is present at 98% by volume and D1 is present at 2% by volume) were vacuum evaporated to thickness. Then, the E1 compound and LiQ were used in a volume ratio of 1:1

After forming the electron transport layer, sequentially evaporating

Lithium fluoride (LiF) and

< example 10>

In example 9, an experiment was performed in the same manner as in example 4 except that compound 4 was used as the hole injection layer and the hole transport layer instead of compound 3 synthesized in production example 4.

< example 11>

In example 9, an experiment was performed in the same manner as above except that HT1 was used instead of compound 3 as the hole injection layer and the hole transport layer, and compound 3 was used instead of HT2 as the hole adjusting layer.

< example 12>

In example 10, an experiment was performed in the same manner as described above except that compound 7 was used as the hole controlling layer instead of compound 3 synthesized in production example 4.

< comparative example 1>

An experiment was performed in the same manner as in example 1 except that HT1 was used as the hole transport layer instead of compound 1 synthesized in production example 2.

< comparative example 2>

In comparative example 1, an experiment was performed in the same manner as above except that HT3 was used instead of HT2 as the hole-regulating layer.

< comparative example 3>

In comparative example 1, an experiment was performed in the same manner as above except that HT4 was used instead of HT1 as the hole transport layer.

< comparative example 4>

In example 11, an experiment was performed in the same manner as described above except that HT2 was used as a hole-regulating layer instead of compound 3 synthesized in production example 4.

< comparative example 5>

An experiment was performed in the same manner as in example 1 except that compound 10 was used as the hole transport layer instead of compound 1 synthesized in production example 2.

< comparative example 6>

An experiment was performed in the same manner as in example 9 except that compound 10 was used as the hole control layer instead of compound 3 synthesized in production example 4.

[ Table 1]

< example 13>

On the ITO transparent electrode thus prepared

The above X1 was thermally vacuum-deposited to form a hole injection layer. Compound 1 as a substance for transporting holes is vacuum-evaporated on the hole injection layer

To form a hole transport layer on which HT2 is used

After forming the hole adjusting layer, the

Bulk H2 and dopant D2(4 wt%) were vacuum evaporated in order of thickness. Then, the E1 compound and LiQ were used in a volume ratio of 1:1

After forming the electron transport layer, sequentially evaporating

Lithium fluoride (LiF) and

Maintenance of lithium fluoride

Aluminum maintenance

The deposition rate of (3).

< example 14>

In example 13, an experiment was performed in the same manner as described above except that compound 3 was used as the hole transport layer instead of compound 1 synthesized in production example 2.

< example 15>

In example 13, an experiment was performed in the same manner as described above except that compound 8 was used as the hole transport layer instead of compound 1 synthesized in production example 2.

< example 16>

On an ITO transparent electrode prepared in the same manner as in example 1

Compound 2 was thermally vacuum-evaporated in thickness to form a hole injection layer, and compound X2 was doped at a doping concentration of 10% (compound 2 was present at 90% by volume and X2 was present at 10% by volume in the layer) to form a hole injection layer

A compound 2 is deposited in a thick vacuum to form a hole transport layer, and a compound 5 is used on the hole transport layer

After forming the hole adjusting layer, the

After forming the electron transport layer, sequentially evaporating

Lithium fluoride (LiF) and

< example 17>

In example 16, an experiment was performed in the same manner as above except that compound 5 was used instead of compound 2 as the hole injection layer and the hole transport layer, and compound 7 was used instead of compound 5 as the hole control layer.

< example 18>

In example 16, an experiment was performed in the same manner as above except that compound 9 was used instead of compound 2 as the hole injection layer and the hole transport layer, and compound 7 was used instead of compound 5 as the hole control layer.

< example 19>

In example 16, an experiment was performed in the same manner as above except that HT1 was used instead of compound 2 as the hole injection layer and the hole transport layer, and compound 6 was used instead of compound 5 as the hole adjusting layer.

< comparative example 5>

In example 13, an experiment was performed in the same manner as described above except that HT1 was used as the hole transport layer instead of compound 1 synthesized in production example 2.

< comparative example 6>

In example 16, an experiment was performed in the same manner as above except that HT1 was used instead of compound 2 as the hole injection layer and the hole transport layer, and HT2 was used instead of compound 5 as the hole adjusting layer.

< comparative example 7>

In example 13, an experiment was performed in the same manner as described above except that compound 10 was used as the hole transport layer instead of compound 1 synthesized in production example 2.

[ Table 2]

As shown in tables 1 and 2, it is understood that the compounds used in examples 1 to 19 are used as a hole injection layer, a hole transport layer, and a hole control layer in an organic light-emitting device, and have a hole transport ability superior to that of other substances, thereby exhibiting low voltage and high efficiency.

Claims

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

chemical formula 1

In the chemical formula 1, the metal oxide is represented by,

q is selected from the following structures:

l1 is a direct bond or is selected from the following structures:

ar1 is hydrogen or is selected from the following structures:

the R 'and R' are the same or different from each other and are each independently an alkyl group having 1 to 40 carbon atoms, a monocyclic aryl group having 6 to 50 carbon atoms, or a polycyclic aryl group having 10 to 40 carbon atoms,

r1 to R6 are hydrogen,

n1 is an integer from 1 to 5,

n2 is an integer from 1 to 5,

n3 is an integer from 1 to 4,

n4 is an integer from 1 to 3,

n5 is an integer from 1 to 3,

n6 is an integer from 1 to 4.

2. The compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formulae 3 to 6:

chemical formula 3

Chemical formula 4

Chemical formula 5

Chemical formula 6

In the chemical formulae 3 to 6,

3. The compound of claim 1, wherein the chemical formula 1 is any one selected from the following compounds:

4. an organic electronic component, comprising: a first electrode, a second electrode provided so as to face the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contain the compound according to any one of claims 1 to 3.

5. The organic electronic element according to claim 4, wherein the organic layer comprises a light-emitting layer containing the compound.

6. The organic electronic element according to claim 4, wherein the organic layer comprises a hole injection layer or a hole transport layer containing the compound.

7. The organic electronic element according to claim 4, wherein the organic layer comprises an electron injection layer or an electron transport layer, and the electron transport layer or the electron injection layer comprises the compound.

8. The organic electronic element according to claim 4, wherein the organic layer comprises an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer comprises the compound.

9. The organic electronic element according to claim 4, wherein the organic electronic element further comprises 1 or 2 or more layers selected from a light-emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

10. The organic electronic element according to claim 4, wherein the organic electronic element is selected from the group consisting of an organic light emitting element, an organic phosphorescent element, an organic solar cell, an Organic Photoreceptor (OPC), and an organic transistor.