CN116583514A - Compound and organic light emitting device comprising the same - Google Patents

Compound and organic light emitting device comprising the same Download PDF

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CN116583514A
CN116583514A CN202280008104.XA CN202280008104A CN116583514A CN 116583514 A CN116583514 A CN 116583514A CN 202280008104 A CN202280008104 A CN 202280008104A CN 116583514 A CN116583514 A CN 116583514A
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车龙范
洪性佶
曹宇珍
李成宰
李炯珍
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LG Chem Ltd
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LG Chem Ltd
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/18—Carrier blocking layers
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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Abstract

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

Description

Compound and organic light emitting device comprising the same
Technical Field
The present application claims priority from korean patent application No. 10-2021-0024908, filed 24 at 2 months of 2021 to the korean patent office, the entire contents of which are incorporated herein.
The present specification relates to a compound and an organic light emitting device including the same.
Background
The organic light emitting device has a structure in which an organic thin film is disposed between 2 electrodes. If a voltage is applied to the organic light emitting device of such a structure, electrons and holes injected from 2 electrodes are combined in an organic thin film to be quenched and emitted light in pairs. The organic thin film may be formed of a single layer or a plurality of layers as required.
As the substance used in the organic light emitting device, a pure organic substance or a complex compound of an organic substance and a metal constituting a complex is largely used, and may be classified into a hole injecting substance, a hole transporting substance, a light emitting substance, an electron transporting substance, an electron injecting substance, and the like according to the purpose. Here, as the hole injecting substance or the hole transporting substance, an organic substance having a p-type property, that is, an organic substance which is easily oxidized and has an electrochemically stable state when oxidized is mainly used. On the other hand, as the electron injecting substance or the electron transporting substance, an organic substance having 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. As the light-emitting layer material, a material having both p-type property and n-type property, that is, a material having a stable form in both the oxidized and reduced states, and a material having high light emission efficiency for converting excitons (exiton) generated by recombination of holes and electrons in the light-emitting layer into light when formed, is preferable.
In order to improve the performance, lifetime, or efficiency of an organic light emitting device, development of materials for organic thin films is continuously required.
Disclosure of Invention
Technical problem
The present specification provides compounds and organic light emitting devices comprising the same.
Solution to the problem
An embodiment of the present specification provides a compound of the following chemical formula 1.
[ chemical formula 1]
In the above-mentioned chemical formula 1,
r1 and R2 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
l1 to L3 are identical to or different from each other and are each independently a direct bond or a substituted or unsubstituted arylene group,
ar1 and Ar2 are the same or different from each other and are each independently a monocyclic aryl group, a substituted or unsubstituted aryl group having 2 or more aromatic rings fused thereto, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted heterocyclic group containing O or S,
however, ar1 and Ar2 are not substituted with a cycloalkyl group, at least one of Ar1 and Ar2 is a substituted or unsubstituted aryl group having 2 or more aromatic rings condensed thereto, or a substituted or unsubstituted fluorenyl group,
a is an integer of 1 to 4, and when a is 2 or more, 2 or more R1 s are each the same or different from each other,
b is an integer of 1 to 4, and when b is 2 or more, 2 or more R2 are each the same or different from each other,
chemical formula 1 above may be substituted with additional deuterium.
Another embodiment of the present specification provides an organic light emitting device, including: a first electrode, a second electrode, and 1 or more organic layers including a light-emitting layer provided between the first electrode and the second electrode, wherein 1 or more of the organic layers include the compound of formula 1.
Effects of the invention
The compound according to an embodiment of the present specification may be used as a material of an organic layer of an organic light emitting device, and by using the compound, an improvement in efficiency, a lower driving voltage, and/or an improvement in lifetime characteristics may be achieved in the organic light emitting device.
In particular, when the compound of the present invention is used for a hole injection layer, a hole transport layer, or an electron blocking layer, the effect of lowering the driving voltage of the device, increasing the efficiency of the device, or increasing the lifetime of the device can be obtained.
Drawings
Fig. 1 to 3 illustrate organic light emitting devices according to some embodiments of the present specification.
1: substrate board
2: first electrode
3: light-emitting layer
4: second electrode
5: hole injection layer
6: hole transport layer
7: light-emitting layer
8: electron transport layer
9: electron blocking layer
10: hole blocking layer
11: electron injection and transport layers.
Detailed Description
The present specification will be described in more detail below.
The present specification provides a compound of the following chemical formula 1.
[ chemical formula 1]
In the above-mentioned chemical formula 1,
r1 and R2 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
l1 to L3 are identical to or different from each other and are each independently a direct bond or a substituted or unsubstituted arylene group,
ar1 and Ar2 are the same or different from each other and are each independently a monocyclic aryl group, a substituted or unsubstituted aryl group having 2 or more aromatic rings fused thereto, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted heterocyclic group containing O or S,
however, ar1 and Ar2 are not substituted with a cycloalkyl group, at least one of Ar1 and Ar2 is a substituted or unsubstituted aryl group having 2 or more aromatic rings condensed thereto, or a substituted or unsubstituted fluorenyl group,
a is an integer of 1 to 4, and when a is 2 or more, 2 or more R1 s are each the same or different from each other,
b is an integer of 1 to 4, and when b is 2 or more, 2 or more R2 are each the same or different from each other,
chemical formula 1 above may be substituted with additional deuterium.
When the compound represented by the above chemical formula 1 is applied to an organic light emitting device, it has effects of a reduction in driving voltage, an improvement in efficiency, and/or an increase in lifetime.
In this specification, when it is stated that a certain member is located "on" another member, it includes not only the case where the certain member is connected to the other member but also the case where another member exists between the two members.
In the present specification, when a certain component is referred to as "including" or "comprising" a certain component, unless otherwise specified, it means that other components may be further included, and not excluded.
Hereinafter, the substituents of the present specification will be described in detail, but are not limited thereto.
In the present specification, the term "represents a site bonded to another substituent or a bond.
In the present specification, 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 it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can be substituted, and when 2 or more substituents are substituted, 2 or more substituents may be the same or different from each other.
In the present specification, the term "substituted or unsubstituted" means substituted with 1 or 2 or more substituents selected from deuterium, halogen group, cyano (-CN), amino, alkoxy, alkyl, aryl and heterocyclic group, or substituted with a substituent in which 2 or more substituents out of the above exemplified substituents are linked, or does not have any substituent. For example, the "substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, biphenyl may be aryl or may be interpreted as a substituent in which 2 phenyl groups are linked.
In the present specification, as examples of the halogen group, there are fluorine (-F), chlorine (-Cl), bromine (-Br) or iodine (-I).
In the present specification, the alkyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples thereof include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl and the like, but are not limited thereto.
In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, for example, an aryl group having 6 to 30 carbon atoms is preferable, and the aryl group may be a single ring or a multiple ring.
When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30. Specifically, the monocyclic aryl group may be phenyl, biphenyl, terphenyl, 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 30. Specifically, the polycyclic aryl group may be naphthyl, anthryl, phenanthryl, triphenylene, pyrenyl, phenalenyl, perylenyl,A group, a fluorenyl group, a fluoranthenyl group, and the like, but is not limited thereto.
In the present specification, the above fluorenyl group may be substituted, and adjacent groups may be bonded to each other to form a ring.
When the fluorenyl group is substituted, the compound may beAnd the like, but is not limited thereto.
In the present specification, the aryl group having 2 or more aromatic rings condensed thereto may be naphthyl, anthryl, phenanthryl, triphenylenyl, pyrenyl, and,A base, etc., but is not limited thereto.
In the present specification, arylene means a group having two bonding positions on an aryl group, i.e., a 2-valent group. These are not limited to the 2-valent groups, and the above description of the aryl groups may be applied.
In this specification, a heterocyclic group contains 1 or more heteroatoms which are non-carbon atoms, and specifically, the heteroatoms may contain 1 or more atoms selected from O, N, S, P and the like. The number of carbon atoms is not particularly limited, but is preferably 1 to 50, more preferably 2 to 30, and the heterocyclic group may be a single ring or a multiple ring. The heterocyclic group may be an aromatic ring, an aliphatic ring, or a ring obtained by fusing them. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,Azolyl, (-) -and (II) radicals>Diazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo->Oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, benzofuranyl, phenanthroline (phenanthrinyl), iso>Oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but are not limited thereto.
In the present specification, a heteroaryl group is an aromatic ring group containing 1 or more heteroatoms which are non-carbon atoms, and specifically, the heteroatoms may contain 1 or more atoms selected from O, N, se, S and the like. The number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to one embodiment, the heteroaryl group has 2 to 30 carbon atoms. Examples of the heteroaryl group may be selected from examples of the heterocyclic group.
In the present specification, cycloalkyl is not particularly limited, but cycloalkyl having 3 to 30 carbon atoms is preferable, specifically, 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 are included, but the present invention is not limited thereto.
In the present specification, the above-mentioned alkoxy group may be a straight chain, branched or cyclic. The carbon number of the alkoxy group is not particularly limited, but is preferably 1 to 30. Specifically, 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-decyloxy and the like are possible, but not limited thereto.
In the present specification, the amine group may be selected from the group consisting of-NH 2 The alkyl amine group, N-alkylaryl amine group, aryl amine group, N-arylheteroaryl amine group, N-alkylheteroaryl amine group and heteroaryl amine group are not particularly limited, but are preferably 0 to 0 carbon atoms 30. Specific examples of the amine group include a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, a phenylamine group, a naphthylamino group, a biphenylamino group, an anthracenylamino group, a 9-methyl-anthracenylamino group, a diphenylamino group, an N-phenylnaphthylamino group, a xylylamino 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-biphenylphenanthrenylamino group, an N-phenylfluorenylamino group, an N-biphenylfluorenylamino group, and the like, but are not limited thereto.
In the present specification, the N-alkylaryl amine group means an amine group in which an alkyl group and an aryl group are substituted on N of the amine group.
In the present specification, an N-arylheteroarylamino group means an amino group substituted with an aryl group and a heteroaryl group on N of the amino group.
In the present specification, an N-alkylheteroarylamino group means an amino group in which an alkyl group and a heteroaryl group are substituted on N of the amino group.
In the present specification, alkyl groups and aryl groups in the alkylamino group, the N-arylalkylamino group, and the N-alkylheteroarylamino group are the same as those exemplified for the alkyl groups and the aryl groups described above.
In the present specification, the hydrogen which may be substituted with additional deuterium means that hydrogen, of which representation is omitted, may be substituted with deuterium.
For example, the compound of formula 1 above may be substituted with additional deuterium means that the phenylene and naphthylene groups of formula 1 may be substituted with additional deuterium.
Specifically, the above chemical formula 1 may be represented by the following chemical formula 1-a.
[ chemical formula 1-A ]
In the above-mentioned chemical formula 1-a,
r1, R2, L1 to L3, ar1, ar2, a and b are as defined in the above chemical formula 1, z1 is an integer of 0 to 4, and z2 is an integer of 0 to 6.
L1 to L3, ar1, ar2, R1 and R2 of the above chemical formulas 1 and 1-a may also contain deuterium, but deuterium is contained in the definition of each substituent, and thus the representation will be omitted.
In one embodiment of the present specification, the chemical formula 1 is the following chemical formula 1-1 or 1-2.
[ chemical formula 1-1]
[ chemical formulas 1-2]
In the above chemical formulas 1-1 and 1-2,
r1, R2, L1 to L3, ar1, ar2, a and b are as defined in the above chemical formula 1,
chemical formulas 1-1 and 1-2 above may be substituted with additional deuterium.
In one embodiment of the present specification, the above chemical formula 1-1 is represented by any one of the following chemical formulas 1-1-1 to 1-1-3.
[ chemical formulas 1-1-1]
[ chemical formulas 1-1-2]
[ chemical formulas 1-1-3]
In the above chemical formulas 1-1-1 to 1-1-3,
r1, R2, L1 to L3, ar1, ar2, a and b are as defined in the above chemical formula 1,
The above chemical formulas 1-1-1 to 1-1-3 may be substituted with additional deuterium.
In one embodiment of the present specification, the above chemical formula 1-2 is represented by any one of the following chemical formulas 1-2-1 to 1-2-3.
[ chemical formula 1-2-1]
[ chemical formulas 1-2-2]
[ chemical formulas 1-2-3]
In the above chemical formulas 1-2-1 to 1-2-3,
r1, R2, L1 to L3, ar1, ar2, a and b are as defined in the above chemical formula 1,
the above chemical formulas 1-2-1 to 1-2-3 may be substituted with additional deuterium.
In one embodiment of the present specification, the phenylene and naphthylene groups of the above formulas 1-1, 1-2, 1-1-1 to 1-1-3 and 1-2-1 to 1-2-3 may be substituted with additional deuterium.
In one embodiment of the present specification, R1 and R2 are the same or different from each other, and each is independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 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 and R2 are the same or different from each other, and each is independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
In one embodiment of the present specification, R1 and R2 are the same or different from each other, and each is independently hydrogen or deuterium.
In one embodiment of the present specification, each of R1 and R2 is hydrogen.
In one embodiment of the present specification, L1 to L3 are the same or different from each other, and each is independently a direct bond, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
In an embodiment of the present specification, the above-mentioned L1 to L3 are the same or different from each other, and each is independently a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted triphenylene group, or a substituted or unsubstituted fluorenylene group.
In one embodiment of the present specification, L1 and L2 are the same or different from each other, and each is independently a direct bond, or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.
In one embodiment of the present specification, the above-mentioned L1 and L2 are the same or different from each other, and each is independently a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted triphenylene group, or a substituted or unsubstituted fluorenylene group.
In one embodiment of the present specification, the above-mentioned L1 and L2 are the same or different from each other, and each is independently a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, or a substituted or unsubstituted naphthylene group.
In one embodiment of the present specification, the above L1 and L2 are the same or different from each other, and each is independently a direct bond, phenylene, biphenylene, terphenylene or naphthylene.
In one embodiment of the present specification, the above L1 and L2 are the same or different from each other, and each is independently a direct bond, phenylene, biphenylene, or naphthylene.
In one embodiment of the present specification, L3 is a directly bonded or substituted or unsubstituted phenylene group.
In one embodiment of the present specification, the L3 is a direct bond or a phenylene group.
In one embodiment of the present specification, the L3 is a direct bond.
In one embodiment of the present specification, ar1 and Ar2 are the same or different from each other, and each is independently a monocyclic aryl group, a substituted or unsubstituted aryl group having 10 to 30 carbon atoms condensed with 2 or more aromatic rings, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms containing O or S.
In one embodiment of the present specification, ar1 and Ar2 are not substituted with cycloalkyl groups, and at least one of Ar1 and Ar2 is a substituted or unsubstituted aryl group having 2 or more aromatic rings condensed thereto, or a substituted or unsubstituted fluorenyl group.
In one embodiment of the present specification, ar1 and Ar2 are the same as or different from each other, and each is independently a monocyclic aryl group; aryl substituted or unsubstituted with an alkyl group, an aryl group, or a heterocyclic group containing O or S, condensed with 2 or more aromatic rings; fluorenyl substituted or unsubstituted with alkyl, aryl, or a heterocyclic group comprising O or S; or a heterocyclic group containing O or S, which is substituted or unsubstituted with an alkyl group, an aryl group, or a heterocyclic group containing O or S.
In one embodiment of the present specification, ar1 and Ar2 are the same or different from each other, and each is independently an aryl group, or an aryl group having 2 or more aromatic rings condensed with a heterocyclic group containing O or S; fluorenyl substituted or unsubstituted with alkyl or aryl; or a heterocyclic group containing O or S.
In an embodiment of the present specification, ar1 and Ar2 are the same or different from each other, and each is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothienyl group, and at least one of Ar1 and Ar2 is a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, or a substituted or unsubstituted fluorenyl group.
In one embodiment of the present specification, ar1 and Ar2 mentioned above are the same or different from each other, and each is independently a phenyl group substituted or unsubstituted with an alkyl group, an aryl group, or a heterocyclic group containing O or S; biphenyl substituted or unsubstituted with alkyl, aryl, or a heterocyclic group containing O or S; terphenyl substituted or unsubstituted with alkyl, aryl, or heterocyclyl containing O or S; naphthyl substituted or unsubstituted with alkyl, aryl, or a heterocyclic group containing O or S; phenanthryl substituted or unsubstituted with alkyl, aryl, or a heterocyclic group containing O or S; triphenylene substituted or unsubstituted with alkyl, aryl, or heterocyclyl containing O or S; fluorenyl substituted or unsubstituted with alkyl, aryl, or a heterocyclic group comprising O or S; dibenzofuranyl substituted or unsubstituted with alkyl, aryl, or heterocyclyl containing O or S; or dibenzothienyl substituted with an alkyl group, an aryl group, or a heterocyclic group containing O or S, at least one of Ar1 and Ar2 is naphthyl substituted with an alkyl group, an aryl group, or a heterocyclic group containing O or S; phenanthryl substituted or unsubstituted with alkyl, aryl, or a heterocyclic group containing O or S; triphenylene substituted or unsubstituted with alkyl, aryl, or heterocyclyl containing O or S; or a fluorenyl group substituted or unsubstituted with an alkyl group, an aryl group, or a heterocyclic group containing O or S.
In one embodiment of the present specification, ar1 and Ar2 are the same or different from each other, and each is independently a phenyl group substituted or unsubstituted with an aryl group or a heterocyclic group containing O or S; biphenyl substituted or unsubstituted with aryl; a terphenyl group; naphthyl substituted or unsubstituted with aryl; phenanthryl; triphenylene; fluorenyl substituted or unsubstituted with alkyl or aryl; dibenzofuranyl; or dibenzothienyl, at least one of Ar1 and Ar2 is naphthyl substituted or unsubstituted with aryl; phenanthryl; triphenylene; or fluorenyl substituted or unsubstituted with alkyl or aryl.
In one embodiment of the present specification, ar1 and Ar2 mentioned above are the same or different from each other, and each is independently a phenyl group substituted or unsubstituted with a naphthyl group, a phenanthryl group, a dibenzofuranyl group or a dibenzothienyl group; biphenyl substituted or unsubstituted with naphthyl or phenanthryl; a terphenyl group; naphthyl substituted or unsubstituted with phenyl or naphthyl; phenanthryl; triphenylene; fluorenyl substituted or unsubstituted with methyl or phenyl; dibenzofuranyl; or dibenzothienyl, at least one of Ar1 and Ar2 is naphthyl, phenanthryl, triphenylenyl substituted or unsubstituted by phenyl or naphthyl, or fluorenyl substituted or unsubstituted by methyl or phenyl.
In one embodiment of the present specification, each of Ar1 and Ar2 is represented by any one of the following structures.
At least one of Ar1 and Ar2 has any one of the following structures.
In the above-described structure, the first and second heat exchangers,
r10 and R11 are substituted or unsubstituted alkyl or substituted or unsubstituted aryl,
the above structures may be substituted with additional deuterium,
- - -is a moiety bonded to chemical formula 1.
In one embodiment of the present specification, the compound of formula 1 may be represented by any one of the following compounds.
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The above compounds may be substituted with additional deuterium.
The compound of chemical formula 1 in the present specification can produce a core structure as shown in the following reaction formula. The substituents may be combined by methods known in the art, and the kinds, positions and number of the substituents may be changed according to techniques known in the art.
< reaction >
In the above reaction formula, L1 to L3, R1, R2, a, b, ar1 and Ar2 are as defined in chemical formula 1.
In this specification, various substituents are introduced into the core structure as described above, whereby compounds having various energy gaps can be synthesized. In the present invention, the HOMO and LUMO levels of the compounds can also be adjusted by introducing various substituents into the core structure of the structure described above.
In addition, by introducing various substituents into the core structure as described above, a compound having the inherent characteristics of the introduced substituents can be synthesized. For example, a substance satisfying the conditions required for each organic layer can be synthesized by introducing substituents mainly used in the hole-injecting substance, the hole-transporting substance, the electron-blocking substance, the light-emitting substance, and the electron-transporting substance used in manufacturing the organic light-emitting device into the above-described core structure.
An embodiment of the present specification provides an organic light emitting device, including: a first electrode, a second electrode, and 1 or more organic layers including a light-emitting layer provided between the first electrode and the second electrode, wherein 1 or more of the organic layers include the compound of formula 1.
The organic light-emitting device of the present specification can be manufactured by a general method and material for manufacturing an organic light-emitting device, except that one or more organic layers are formed using the above-described compound.
The compound may be used not only in the vacuum vapor deposition method but also in the solution coating method to form an organic layer in the production of an organic light-emitting device. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spray coating, roll coating, and the like, but is not limited thereto.
For example, the organic light emitting device of the present specification may be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. This can be manufactured as follows: a first electrode is formed by vapor deposition of a metal or a metal oxide having conductivity or an alloy thereof on a substrate by a physical vapor deposition method (PVD: physical vapor deposition (physical Vapor Deposition)) such as sputtering or electron beam evaporation, then an organic layer including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, and an electron transport layer is formed on the first electrode, and then a substance usable as a second electrode is vapor deposited on the organic layer. In addition to this method, the second electrode material, the organic layer, and the first electrode material may be sequentially deposited on the substrate to manufacture an organic light-emitting device. In addition, the compound of chemical formula 1 may be formed into an organic layer not only by a vacuum deposition method but also by a solution coating method in the production of an organic light-emitting device. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, roll coating, and the like, but is not limited thereto.
In one embodiment of the present specification, the organic layer may be formed of a single-layer structure or a multilayer structure in which 2 or more organic layers are stacked. When the organic light emitting device includes a plurality of organic layers, for example, the organic layers may have a multi-layer structure including a hole injection layer, a hole transport layer, a layer that performs hole injection and hole transport simultaneously, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, a layer that performs electron injection and electron transport simultaneously, and the like. However, the structure of the organic light emitting device is not limited thereto, and may include a smaller or larger number of organic layers.
The organic layers may be formed of the same material or different materials. The organic layer may be formed into a smaller number of layers by a solvent process (solvent process) other than vapor deposition, such as spin coating, dip coating, knife coating, screen printing, ink jet printing, or thermal transfer printing, using various polymer materials.
In one embodiment of the present disclosure, a plurality of organic layers are provided between the first electrode and the light-emitting layer, and the organic layer on the side close to the light-emitting layer contains the compound.
In one embodiment of the present disclosure, 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 disclosure, the organic layer includes a hole injection layer, a hole transport layer, or an electron blocking layer, and the hole injection layer, the hole transport layer, or the electron blocking layer includes the compound.
In one embodiment of the present disclosure, the light-emitting layer includes the compound.
In an embodiment of the present specification, the light emitting layer may include the compound as a dopant of the light emitting layer.
In one embodiment of the present disclosure, the light-emitting layer may include the compound as a dopant of the light-emitting layer, and may further include a host.
In one embodiment of the present disclosure, the light-emitting layer includes the compound as a dopant of the light-emitting layer, a fluorescent host or a phosphorescent host, and other organic compounds, metals, or metal compounds as dopants.
In one embodiment of the present disclosure, the light-emitting layer includes the compound as a dopant of the light-emitting layer, and further includes a fluorescent host or a phosphorescent host, and may be used together with an iridium (Ir) dopant.
In one embodiment of the present specification, the light-emitting layer may include the compound as a host of the light-emitting layer.
In one embodiment of the present disclosure, the light-emitting layer may include the compound as a host of the light-emitting layer, and may further include a dopant.
In one embodiment of the present disclosure, the organic layer includes an electron blocking layer, and the electron blocking layer includes the compound.
In one embodiment of the present disclosure, the organic light emitting device includes a first electrode, a second electrode, and a light emitting layer disposed between the first electrode and the second electrode, wherein a single organic layer is further disposed between the light emitting layer and the first electrode, and the organic layer includes the compound.
In one embodiment of the present disclosure, the organic light-emitting device includes a first electrode, a second electrode, and a light-emitting layer provided between the first electrode and the second electrode, wherein a plurality of organic layers are further provided between the light-emitting layer and the first electrode, and 1 or more of the organic layers contain the compound.
In one embodiment of the present disclosure, the organic light emitting device includes a first electrode, a second electrode, and a light emitting layer disposed between the first electrode and the second electrode, wherein 1 or more layers of a hole injection layer, a hole transport layer, and an electron blocking layer are further included between the light emitting layer and the first electrode, and 1 or more layers of the hole injection layer, the hole transport layer, and the electron blocking layer contain the compound.
In one embodiment of the present disclosure, the organic light emitting device includes a first electrode, a second electrode, and a light emitting layer disposed between the first electrode and the second electrode, wherein the first electrode and the light emitting layer include a hole injection layer, a hole transport layer, and an electron blocking layer, and 1 or more of the hole injection layer, the hole transport layer, and the electron blocking layer include the compound.
In one embodiment of the present specification, the organic light-emitting device is configured such that a first electrode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, and a second electrode are sequentially provided, and 1 or more layers of the hole injection layer, the hole transport layer, and the electron blocking layer contain the compound. At this time, an additional organic layer may be disposed between the above layers.
In one embodiment of the present specification, the organic light-emitting device is a structure in which a first electrode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, and a second electrode are sequentially stacked, and the hole injection layer, the hole transport layer, or the electron blocking layer contains the compound.
In an embodiment of the present disclosure, an additional organic layer may be further included between the light emitting layer and the second electrode. For example, one or more layers selected from a hole blocking layer, an electron injection layer, an electron transport layer, and a layer that performs electron injection and electron transport simultaneously may be further included between the light-emitting layer and the second electrode.
In one embodiment of the present invention, the organic light-emitting device is configured such that a first electrode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron injection and transport layer, and a second electrode are sequentially stacked, and 1 or more of the hole injection layer, the hole transport layer, and the electron blocking layer contain the compound.
In one embodiment of the present specification, the organic light emitting device is a structure in which a first electrode, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron injection and transport layer, and a second electrode are sequentially stacked, and the hole injection layer, the hole transport layer, or the electron blocking layer contains the compound.
In one embodiment of the present specification, the organic light emitting device is a structure in which a first electrode, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron injection and transport layer, and a second electrode are sequentially stacked, and the electron blocking layer includes the compound.
In one embodiment of the present disclosure, the first electrode is an anode, and the second electrode is a cathode.
According to another embodiment, the first electrode is a cathode, and the second electrode is an anode.
For example, the structure of the organic light emitting device of the present specification may have the structure shown in fig. 1 to 3, but is not limited thereto.
Fig. 1 illustrates an example of an organic light emitting device constituted by a substrate 1, a first electrode 2, a light emitting layer 3, and a second electrode 4.
Fig. 2 illustrates an example of an organic light-emitting device constituted by a substrate 1, a first electrode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron transport layer 8, and a second electrode 4.
Fig. 3 illustrates an example of an organic light-emitting device constituted by the substrate 1, the first electrode 2, the hole injection layer 5, the hole transport layer 6, the electron blocking layer 9, the light-emitting layer 7, the hole blocking layer 10, the electron injection and transport layer 11, and the second electrode 4.
Specifically, the organic light emitting device may have a laminated structure as described below, for example, in addition to the structure explicitly shown in the drawings, but is not limited thereto.
(1) Anode/hole transport layer/light emitting layer/cathode
(2) Anode/hole injection layer/hole transport layer/light emitting layer/cathode
(3) Anode/hole transport layer/light emitting layer/electron transport layer/cathode
(4) Anode/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(5) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/cathode
(6) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(7) Anode/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/cathode
(8) Anode/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/electron injection layer/cathode
(9) Anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/cathode
(10) Anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/electron injection layer/cathode
(11) Anode/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/cathode
(12) Anode/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode
(13) Anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/cathode
(14) Anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode
(15) Anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/hole blocking layer/cathode for simultaneous electron injection and electron transport
In an embodiment of the present specification, the above-described "electron transport layer/electron injection layer" may be replaced by "electron injection and transport layer" or "layer that performs electron injection and electron transport simultaneously".
In an embodiment of the present specification, the "hole injection layer/hole transport layer" described above may be replaced by "hole injection and transport layer" or "layer that performs hole injection and hole transport simultaneously".
In an embodiment of the present specification, the hole transport layer may be formed of a multilayer structure. For example, it may be constituted of a first hole transport layer and a second hole transport layer containing substances different from each other.
The anode is an electrode for injecting holes, and is preferably a substance having a large work function as an anode substance in order to allow holes to be smoothly injected into the organic layer. Examples of the anode material include vanadium, chromium, copper, zinc, and goldAn isopmetal or an alloy thereof; metal oxides such as zinc Oxide, indium Tin Oxide (ITO), and Indium zinc Oxide (IZO, indium Zinc Oxide); znO of Al or SnO 2 A combination of metals such as Sb and the like and oxides; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene ]Conductive polymers such as (PEDOT), polypyrrole and polyaniline, but not limited thereto.
The cathode is an electrode for injecting electrons, and is preferably a substance having a small work function as a cathode substance in order to facilitate injection of electrons into the organic layer. Examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; liF/Al or LiO 2 And/or Al, but is not limited thereto.
The hole injection layer is a layer that can function to smooth injection of holes from the anode to the light-emitting layer. The hole injecting substance is a substance that can well inject holes from the anode at a low voltage, and preferably, a HOMO (highest occupied molecular orbital ) of the hole injecting substance is interposed between a work function of the anode substance and a HOMO of a surrounding organic layer. Examples of the hole injection substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophene, arylamine-based compounds, hexanitrile hexaazabenzophenanthrene-based compounds, quinacridone-based compounds, perylene-based compounds, benzonitrile-based compounds, anthraquinone, polyaniline, and polythiophene-based conductive polymers. Specifically, an arylamine compound and a benzonitrile compound can be used for the hole injection layer. More specifically, a benzonitrile compound substituted with a halogen group and an arylamine compound substituted with a carbazole group may be used, but are not limited thereto. The thickness of the hole injection layer may be 1 to 150nm. When the thickness of the hole injection layer is 1nm or more, there is an advantage that the degradation of the hole injection characteristic can be prevented, and when the thickness of the hole injection layer is 150nm or less, there is an advantage that the increase of the driving voltage for improving the migration of holes can be prevented.
The hole transport layer can function to smooth the transport of holes. The hole-transporting substance is a substance capable of receiving holes from the anode or the hole-injecting layer and transferring the holes to the light-emitting layer, and a substance having a large mobility to the holes is suitable. For example, the hole-transporting substance includes, but is not limited to, an arylamine compound, a carbazole compound, a conductive polymer, and a block copolymer having both a conjugated portion and a non-conjugated portion. Specifically, the hole transport layer may be formed using a carbazole-based compound substituted with an arylamine group, but is not limited thereto.
A hole buffer layer may be further disposed between the hole injection layer and the hole transport layer, and may include a hole injection or transport material known in the art.
An electron blocking layer may be provided between the hole transport layer and the light emitting layer. The electron blocking layer may use the above-mentioned compound or a material known in the art.
The light-emitting layer may emit red, green, or blue light, and may be made of a phosphorescent material or a fluorescent material. The light-emitting substance is a substance capable of receiving holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combining them to emit light in the visible light region, and is preferably a substance having high quantum efficiency for fluorescence or phosphorescence. For example, the above-mentioned luminescent material may be 8-hydroxyquinoline aluminum complex (Alq 3 ) The method comprises the steps of carrying out a first treatment on the surface of the Carbazole-based compounds; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (E) benzo (EAzole, benzothiazole, and benzimidazole compounds; poly (p-phenylene vinylene) (PPV) based polymers; spiro (spiro) compounds; polyfluorene, rubrene, and the like, but is not limited thereto.
Examples of the host material of the light-emitting layer include an aromatic condensed ring derivative and a heterocyclic compound. For example, as the aromatic condensed ring derivative, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, as the heterocyclic ring-containing compoundThe compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compoundsPyrimidine derivatives, and the like, but are not limited thereto. Specifically, as the main body of the light-emitting layer, an anthracene derivative can be used, but is not limited thereto.
When the light-emitting layer emits red light, as a light-emitting dopant, a phosphorescent substance such as PIQIr (acac) (bis (1-phenylisoquinoline) acetylacetonate iridium, bis (1-phenylisoquinoline) acetylacetonate iridium), PQIr (acac) (bis (1-phenylquinoline) acetylacetonate iridium, bis (1-phenylquinoline) acetylacetonate iridium), PQIr (tris (1-phenylquinoline) iridium, tris (1-phenylquinoline) iridium), ptOEP (platinum octaethylporphyrin, octaethylporphyrin platinum), or Alq may be used 3 Fluorescent substances such as tris (8-hydroxyquinoline) aluminum, etc., but are not limited thereto. When the light emitting layer emits green light, ir (ppy) can be used as a light emitting dopant 3 (tris (2-phenylpyridine) iridium), tris (2-phenylpyridine) iridium) or the like, or Alq 3 And the like, but is not limited thereto. When the light-emitting layer emits blue light, as the light-emitting dopant, (4, 6-F 2 ppy) 2 Examples of the fluorescent substance include, but are not limited to, phosphorescent substances such as Irpic, fluorescent substances such as spiro-DPVBi (spiro-DPVBi), spiro-6P (spiro-6P), distyrylbenzene (DSB), distyrylarylene (DSA), pyrene-based compounds, PFO-based polymers, and PPV-based polymers. Specifically, as the dopant, a pyrene compound may be used, but is not limited thereto.
A hole blocking layer may be disposed between the electron transport layer and the light emitting layer. The hole blocking layer is a layer that prevents holes from reaching the cathode, and can be formed under the same conditions as the hole injection layer. For example, as a substance suitable for use in the hole blocking layer, there isDiazole derivatives or triazole derivatives, triazine derivatives, phenanthroline derivatives, BCP and aluminum complexesA compound (aluminum complex), etc., but is not limited thereto. Specifically, a triazine derivative may be used, but is not limited thereto.
The electron transport layer can play a role in enabling electron transport to be smooth. The electron transporting substance is a substance that can well receive electrons from the cathode and transfer them to the light-emitting layer, and is suitable for a substance having high mobility of electrons. For example, the electron-transporting substance may be an Al complex of 8-hydroxyquinoline or an Al complex containing Alq 3 But not limited to, complexes of (c) and (d), organic radical compounds, hydroxyflavone-metal complexes, and the like. The thickness of the electron transport layer may be 1 to 50nm. When the thickness of the electron transport layer is 1nm or more, there is an advantage that the degradation of the electron transport property can be prevented, and when it is 50nm or less, there is an advantage that the increase of the driving voltage for the purpose of improving the electron transfer can be prevented when the thickness of the electron transport layer is too thick.
The electron injection layer can perform a function of smoothly injecting electrons. As the electron injecting substance, the following compounds are preferable: a compound which has an ability to transport electrons, an effect of injecting electrons from a cathode, an excellent electron injection effect for a light-emitting layer or a light-emitting material, prevents excitons generated in the light-emitting layer from migrating to a hole injection layer, and has excellent thin film forming ability. Examples of the electron-injecting substance include fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like, Azole,/->The diazoles, triazoles, triazines, imidazoles, perylenetetracarboxylic acids, fluorenylenemethanes, anthrones, and the like, and their derivatives, metal complexes, and nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
Examples of the metal complex include, but are not limited to, lithium 8-hydroxyquinoline, zinc bis (8-hydroxyquinoline), copper bis (8-hydroxyquinoline), manganese bis (8-hydroxyquinoline), aluminum tris (2-methyl-8-hydroxyquinoline), gallium tris (8-hydroxyquinoline), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), gallium chloride bis (2-methyl-8-quinoline) (o-cresol) gallium, aluminum bis (2-methyl-8-quinoline) (1-naphthol), gallium bis (2-methyl-8-quinoline) (2-naphthol).
The electron transport layer and the electron injection layer may be formed of a single layer. For example, the electron injection and transport layer may be formed by vacuum evaporation of the electron injection material and the electron transport material simultaneously. The electron injection and transport layer may further comprise a metal complex. Examples of the metal complex include Al complexes of 8-hydroxyquinoline (Alq 3 ) LiQ, metal complex, etc., but is not limited thereto. For example, the above electron injection and transport layer may use triazine derivatives and lithium quinoline (LiQ), but is not limited thereto.
The organic light emitting device according to the present application may be of a top emission type, a bottom emission type, or a bi-directional emission type, depending on the materials used.
Modes for carrying out the application
In the following, experimental examples will be described in detail for the purpose of specifically describing the present specification. However, the embodiments according to the present specification may be modified into various forms, and the scope of the present application is not to be construed as being limited to the embodiments described in detail below. Embodiments of the present application are provided to more fully explain the present description to those skilled in the art.
Production example 1.
After 9- (3- (4-chloronaphthalen-1-yl) phenyl) -9H-carbazole (9- (3- (4-chlororhodophthyl-1-yl) phenyl) -9H-carbazole) (8.34 g,20.64 mmol) and a3 (8.20 g,22.71 mmol) were completely dissolved in 260mL of xylene in a 500mL round bottom flask, naOtBu (Sodium tert-butoxide) (2.98 g,30.97 mmol) was added and Bis (tri-tert-butylphosphine) palladium (0) (Bis (tris-tert-butylphosphine) palladium (0)) (0.21 g,0.42 mmol) was added and the mixture was heated and stirred for 5 hours. After the temperature was lowered to room temperature and the base (base) was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 270mL of ethyl acetate to give compound 1 (10.14 g, yield: 67%).
MS[M+H] + ＝729
Production example 2.
After complete dissolution of compound 9- (3- (4-chloronaphthalen-1-yl) phenyl) -9H-carbazole (7.46 g,18.47 mmol) and compound a8 (8.02 g,20.31 mmol) in 270mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (2.66 g,27.70 mmol) was added and bis (tri-t-butylphosphine) palladium (0) (0.19 g,0.37 mmol) was added and heated for 3 hours with stirring. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 250mL of ethyl acetate to give Compound 2 (11.05 g, yield: 78%).
MS[M+H] + ＝763
Production example 3.
After complete dissolution of compound 9- (3- (4-chloronaphthalen-1-yl) phenyl) -9H-carbazole (5.50 g,13.61 mmol) and compound a1 (7.26 g,14.98 mmol) in 260mL of xylene under nitrogen in a 500mL round bottom flask, naOtBu (1.70 g,17.70 mmol) was added and bis (tri-t-butylphosphine) palladium (0) (0.21 g,0.41 mmol) was added and heated to stir for 4 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 280mL of ethyl acetate to give Compound 3 (8.53 g, yield: 73%).
MS[M+H] + ＝854
Preparation example 4.
After complete dissolution of compound 9- (3- (4-chloronaphthalen-1-yl) phenyl) -9H-carbazole (5.50 g,13.61 mmol) and compound a4 (6.66 g,14.98 mmol) in 260mL of xylene under nitrogen in a 500mL round bottom flask, naOtBu (1.70 g,17.70 mmol) was added and bis (tri-t-butylphosphine) palladium (0) (0.21 g,0.41 mmol) was added and heated to stir for 4 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 280mL of ethyl acetate to give Compound 4 (7.22 g, yield: 65%).
MS[M+H] + ＝814
Production example 5.
After complete dissolution of compound 9- (3- (4-chloronaphthalen-1-yl) phenyl) -9H-carbazole (5.50 g,13.61 mmol) and compound a5 (6.29 g,14.98 mmol) in 260mL of xylene under nitrogen in a 500mL round bottom flask, naOtBu (1.70 g,17.70 mmol) was added and bis (tri-t-butylphosphine) palladium (0) (0.21 g,0.41 mmol) was added and heated to stir for 5 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 250mL of ethyl acetate to give Compound 5 (6.97 g, yield: 65%).
MS[M+H] + ＝789
Preparation example 6.
After complete dissolution of compound 9- (3- (4-chloronaphthalen-1-yl) phenyl) -9H-carbazole (5.50 g,13.61 mmol) and compound a6 (6.75 g,14.98 mmol) in 260mL of xylene in a 500mL round bottom flask under nitrogen atmosphere, naOtBu (1.70 g,17.70 mmol) was added and bis (tri-t-butylphosphine) palladium (0) (0.21 g,0.42 mmol) was added and heated to stir for 4 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 240mL of ethyl acetate to give Compound 6 (7.11 g, yield: 64%).
MS[M+H] + ＝820
Preparation example 7.
After complete dissolution of compound 9- (3- (4-chloronaphthalen-1-yl) phenyl) -9H-carbazole (5.50 g,13.61 mmol) and compound a7 (6.99 g,14.98 mmol) in 260mL of xylene under nitrogen in a 500mL round bottom flask, naOtBu (1.70 g,17.70 mmol) was added and bis (tri-t-butylphosphine) palladium (0) (0.21 g,0.41 mmol) was added and heated to stir for 4 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 250mL of ethyl acetate to give Compound 7 (7.86 g, yield: 69%).
MS[M+H] + ＝836
Example 1.
ITO (indium tin oxide) toThe glass substrate coated to have a thin film thickness is put into distilled water in which a detergent is dissolved, and washed with ultrasonic waves. In this case, a product of fei he er (Fischer co.) was used as the detergent, and distilled water was filtered twice using a Filter (Filter) manufactured by millbore co. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the distilled water washing is completed, ultrasonic washing is performed by using solvents of isopropanol, acetone and methanol, and the obtained product is dried and then conveyed to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transferred to a vacuum vapor deposition machine.
On the ITO transparent electrode as an anode thus prepared, the following compound HI1 and the following compound HI2 were mixed in a ratio of 98:2 (molar ratio)And performing thermal vacuum evaporation to form a hole injection layer. On the hole injection layer, a compound represented by the following formula HT1 is added>Vacuum evaporation is performed to form a hole transport layer. Next, on the hole transport layer, the film thickness is +. >The compound 1 produced in production example 1 was vacuum-evaporated to form an electron blocking layer. Next, on the above electron blocking layer, the film thickness is +.>The following compound BH and the following compound BD were vacuum-evaporated at a weight ratio of 25:1 to form a light-emitting layer. On the above-mentioned light-emitting layer, the film thickness is +.>The hole blocking layer was formed by vacuum evaporation of the following compound HB 1. Next, on the hole blocking layer, the following compound ET1 and the following compound LiQ were vacuum evaporated at a weight ratio of 1:1, thereby forming ∈1>Form an electron injection and transport layer. On the electron injection and transport layer, lithium fluoride (LiF) is sequentially added +.>Is made of aluminum +.>And the thickness of the metal layer is evaporated to form a cathode. />
In the above process, the vapor deposition rate of the organic matter is maintainedTo->Lithium fluoride maintenance of cathodeIs kept at>Is to maintain a vacuum degree of 2x10 during vapor deposition -7 To 5x10 -6 The support is thus fabricated into an organic light emitting device.
Examples 2 to 7.
An organic light emitting device was manufactured in the same manner as in example 1, except that the compound described in table 1 below was used instead of the compound 1 in example 1.
Comparative examples 1 to 18.
An organic light emitting device was manufactured in the same manner as in example 1 above, except that the compound described in table 1 below was used instead of the compound 1 in example 1 above. The compounds of EB2 to EB19 used in table 1 below are shown below.
/>
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When a current was applied to the organic light emitting devices manufactured in the above examples and comparative examples, voltage, efficiency, color coordinates, and lifetime were measured, and the results thereof are shown in table 1 below. T95 represents the time required for the luminance to decrease from the initial luminance (1600 nit) to 95%.
TABLE 1
As shown in table 1 above, the organic light emitting device using the compound of the present invention as an electron blocking layer shows excellent characteristics in terms of efficiency, driving voltage, and stability of the organic light emitting device.
In contrast, the organic light emitting device using the compound other than chemical formula 1 as an electron blocking layer exhibits characteristics of an increase in driving voltage, a decrease in efficiency, and a decrease in lifetime.
Specifically, comparative examples 1 to 15, in which compounds (EB 2 to EB4, EB6 and EB 7) having different substitution positions of the phenylene group bonded to the phenylene group of chemical formula 1, compounds (EB 5) in which Ar1 or Ar2 of chemical formula 1 is an N-containing heterocyclic group, compounds (EB 8 and EB 9) having phenylene group and amine group substituted on rings different from each other on the phenylene group of chemical formula 1, compounds (EB 10 and EB 11) in which Ar1 or Ar2 of chemical formula 1 is substituted with a cycloalkyl group, compounds (EB 12 to EB 14) in which phenylene group is substituted with an additional substituent (other than deuterium) in chemical formula 1, compounds (EB 15 and EB 16) having phenylene group in place of the naphthalene group in chemical formula 1, and compounds (EB 17, EB18 and EB 19) in which Ar1 and Ar2 are each other are not fused with an aryl group of 2 or more aromatic rings, and substituted or unsubstituted fluorenyl group, show characteristics of an increase in driving voltage, a reduction in efficiency, and a lifetime, as compared with examples 1 and 2.
While the preferred embodiment (electron blocking layer) of the present invention has been described above, the present invention is not limited thereto, and it is also within the scope of the present invention to be modified and implemented in various forms within the scope of the invention as claimed and the detailed description of the invention.

Claims (11)

1. A compound of the following chemical formula 1:
[ chemical formula 1]
In the chemical formula 1 described above, a compound having the formula,
r1 and R2 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
l1 to L3 are identical to or different from each other and are each independently a direct bond or a substituted or unsubstituted arylene group,
ar1 and Ar2 are the same or different from each other and are each independently a monocyclic aryl group, a substituted or unsubstituted aryl group having 2 or more aromatic rings fused thereto, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted heterocyclic group containing O or S,
however, ar1 and Ar2 are not substituted by cycloalkyl, at least one of Ar1 and Ar2 is a substituted or unsubstituted aryl group having 2 or more aromatic rings condensed thereto, or a substituted or unsubstituted fluorenyl group,
a is an integer of 1 to 4, and when a is 2 or more, 2 or more R1 are each the same or different from each other,
b is an integer of 1 to 4, and when b is 2 or more, 2 or more R2 are each the same or different from each other,
the chemical formula 1 is optionally substituted with additional deuterium.
2. The compound of claim 1, wherein L1 to L3 are the same or different from each other and are each independently a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted triphenylene group, or a substituted or unsubstituted fluorenylene group.
3. The compound according to claim 1, wherein Ar1 and Ar2 are the same or different from each other and are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group,
At least one of Ar1 and Ar2 is a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, or a substituted or unsubstituted fluorenyl group.
4. The compound of claim 1, wherein Ar1 and Ar2 are the same or different from each other, each independently being a monocyclic aryl group; aryl substituted or unsubstituted with an alkyl group, an aryl group, or a heterocyclic group containing O or S, condensed with 2 or more aromatic rings; fluorenyl substituted or unsubstituted with alkyl, aryl, or a heterocyclic group comprising O or S; or a heterocyclic group containing O or S which is substituted or unsubstituted with an alkyl group, an aryl group, or a heterocyclic group containing O or S,
at least one of Ar1 and Ar2 is an aryl group substituted or unsubstituted with an alkyl group, an aryl group, or a heterocyclic group containing O or S, to which 2 or more aromatic rings are fused; or a fluorenyl group substituted or unsubstituted with an alkyl group, an aryl group, or a heterocyclic group containing O or S.
5. The compound of claim 1, wherein at least one of Ar1 and Ar2 is any one of the following structures:
in the case of the construction described above, in which the first and second support members are arranged,
r10 and R11 are substituted or unsubstituted alkyl or substituted or unsubstituted aryl,
The structure is optionally substituted with additional deuterium,
is a moiety that binds to chemical formula 1.
6. The compound of claim 1, wherein the chemical formula 1 is the following chemical formula 1-1 or 1-2:
[ chemical formula 1-1]
[ chemical formulas 1-2]
In the chemical formulas 1-1 and 1-2,
r1, R2, L1 to L3, ar1, ar2, a and b are as defined in the chemical formula 1,
the chemical formulas 1-1 and 1-2 are optionally substituted with additional deuterium.
7. The compound according to claim 6, wherein the chemical formula 1-1 is any one of the following chemical formulas 1-1-1 to 1-1-3:
[ chemical formulas 1-1-1]
[ chemical formulas 1-1-2]
[ chemical formulas 1-1-3]
In the chemical formulas 1-1-1 to 1-1-3,
r1, R2, L1 to L3, ar1, ar2, a and b are as defined in the chemical formula 1,
the chemical formulas 1-1-1 to 1-1-3 are optionally substituted with additional deuterium.
8. The compound according to claim 6, wherein the chemical formula 1-2 is any one of the following chemical formulas 1-2-1 to 1-2-3:
[ chemical formula 1-2-1]
[ chemical formulas 1-2-2]
[ chemical formulas 1-2-3]
In the chemical formulas 1-2-1 to 1-2-3,
r1, R2, L1 to L3, ar1, ar2, a and b are as defined in formula 1, and the formulas 1-2-1 to 1-2-3 are optionally substituted with additional deuterium.
9. The compound of claim 1, wherein the compound of formula 1 is any one of the following structures:
the structure is optionally substituted with additional deuterium.
10. An organic light emitting device, comprising: a first electrode, a second electrode, and 1 or more organic layers including a light-emitting layer provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains the compound according to any one of claims 1 to 9.
11. The organic light-emitting device of claim 10, wherein the organic layer comprises a hole injection layer, a hole transport layer, or an electron blocking layer, the hole injection layer, the hole transport layer, or the electron blocking layer comprising the compound.
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